


stop thinking you're the only option

by theedgeofthedesert



Category: Gilmore Girls
Genre: Alternate Universe - Canon Divergence, F/M
Language: English
Status: In-Progress
Published: 2016-12-08
Updated: 2017-01-28
Packaged: 2018-09-07 06:43:29
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 15
Words: 64,582
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8787691
Author URL: https://archiveofourown.org/users/theedgeofthedesert/pseuds/theedgeofthedesert
Summary: Alternate universe. An older, more stable 23 year old Jess Mariano meets a 19 year old Rory Gilmore on the verge of a series of life altering mistakes after her freshman year at Yale. Their meeting sparks a divergent path for the both of them.





	1. Chapter 1

**Author's Note:**

> I don’t quite know where I’m going with this. This is born out of many a discussion on the Gilmore Girls subreddit surrounding our dear Rory and the progression of her personality. I think we can all agree that a tragedy of Rory and Jess is timing and so I wonder what could come about if we live in a world where that’s not necessarily an issue? What they're at a point where the versions of themselves work towards good for the both of them.
> 
> This story takes place in at the end of season 4 but it’s AU where 1. Rory and Jess have not met up until this point and 2. Jess is older (22 or 23, I haven’t decided to be honest). But if you want a sense of where he’s at, think of our boy at season 6.
> 
> Your feedback is always appreciated, let me know if I’m absolutely insane especially because this is getting me back into the fic writing game.

Jess felt he was getting soft in his old age.

5 years ago you could not have paid him to be here walking his crazy mother down the aisle towards her equally crazy and kind of dimwitted husband but he supposes that now change is good. He certainly has every right to stay angry at Liz for the rest of his life. She was never the greatest mother and spent more time high and drunk with a string of men than any on his well being. When he was 18 and able to run off to do his own thing he set off to figure out what his life was supposed to look like. Fuck graduating from high school since he didn’t like going anyway. Instead he figured out where his biological father lived and set off on a road trip to California from New York City the day after he turned 18. He wanted answers and once he got those answers he would figure it from there. 

Venice Beach was nothing he wanted. He was a complete fish out of water from the sand creeping up his into his dark jeans to the heat stifling him in the leather jacket he didn’t go anywhere without. And when he eventually found his father Jimmy Mariano, he also found a warm and sarcastic pseudo stepmother named Sasha and an 11 year old hiding expert bookworm named Lily. 

He was pissed at first.

Jimmy had the gall to not even stick around long enough to cut the umbilical cord when he was born, but he had time to give Lily a nickname that he affectionately called her while ruffling her hair? It was maddening. But at least Jimmy looked guilty about it.

He worked at the hot dog stand that spring and summer, saving money to make it back east. He picked Lily up from school everyday and would read with her on the boardwalk. He helped Sasha feed the dogs at night even though about 3 of them always seemed to almost bite his hand off. He and Jimmy would never be perfect and there would never be full forgiveness but he got his answers. And he also got his inspiration.

He wrote The Subsect during that time in California. He would usually end up on the beach at night which was the only time he would even consider it to be worth it. It felt like therapy and as corny as it sounds the anger and resentment slowly resolved itself the more he wrote on the pages of his notebook. By the end of the summer he had finished it and he felt like his time on the West Coast was over.

His goodbye to Jimmy was simple, Sasha made him promise to come and visit again within the next year, and Lily made him promise to mention her whenever he got his book published. He didn’t think it was going to happen at the time, but when it did he kept his promise. 

Jess traveled through the United States again back to the east coast and plotted his next move. Once he reached Chicago he knew 2 things: New York was not only expensive but also full of memories good and bad that he didn’t know he could move beyond if he went back there. His mother was there and that in and of itself was a motivator to stay the hell away. 2. New York was expensive and he had to be at least a little realistic about his prospects. He didn’t have his high school diploma and at best could be doing odd jobs to make ends meet. He needed a city that was for sure but he also needed to live.

So he headed to Philadelphia.

He found a cheap place in South Philly and started working in a diner during the day and a bar at night. The bar is where he met Matt and Chris.

The two of them showed up to South Philly Taproom a few times a week to shoot the shit and bug the hell out of Jess. They knew right away that he was not only new to the bar but also to the city so they took great joy in annoying the hell out of him and citing it as his initiation. Eventually he started biting back and they enjoyed his wit so they invited him to sit down with them during his break. From there they told him all about the small publishing house they started on Locust St in Fitler Square. On a whim when drunk with them after his shift he mentioned that he’d written something, an admission they did not forget the next day when they showed up to the Broad Street Diner to hassle him and demand to see his manuscript in hopes that it would be good enough for them to publish it. They followed him everywhere, relentless and unwilling to give until they were able to see what he wrote. He finally relented one night after a shift at SPTR when they followed him back to his apartment and shouted obscenities where he could hear from his window. It was merciful really, his neighbors were so close to coming out there and ending their lives.

They loved it, but Jess still didn’t think it was that good. But Chris and Matt didn’t seem like the type to dick around on him and just tell him his novel was worth publishing if it wasn’t. So they did and hired him to work there along the way. He was able to quit his job at the diner, of course the one he liked least. They printed 500 copies of his book for him to sell at independent bookstores along the coast. It was hard work he would never make a lot of money for, but in the end he was a published author and that meant something.

From that point he built a life in Philadelphia. He continued to work at SPTR for another year until things picked up at Truncheon enough that he could afford to have that be his sole income. He reluctantly accepted that Chris and Matt were his best friends who were determined to break him out of his shells and defenses that were bitterness and resentment. Nights spent at Dirty Franks and other dive bars in the city slowly melted his exterior. He would spend his Saturdays exploring the different neighborhoods in the city, writing his second novel while sitting on the El gaining inspiration from the Mural Arts route. He dated, never wanting to put down long term roots with a girl but slowly finding that he was capable of doing so.

He wasn’t perfect, but at 23 he was certainly less angry and was therefore a tad more accepting when his mother called him to tell him she was getting married and needed him to walk her down the aisle.

The wedding was in Stars Hollow, a small town in Connecticut that Liz has threatened to send Jess during his wildest moments until the next morning when she would forget and he would run away to a friend’s house for a few days so that she couldn’t make good on his promise. As he looks around at the town square and cringes at the overwhelming sense of Pleasantville he gets as he walks around. So far the owner of the market has been eying him as if he’s about to start a violent riot and the bigger woman who apparently owns the dance studio eyes him as if she’s going to kidnap him and keep him to herself for the rest of his life.

He doesn’t really know what to make of it.

The only thing that seems to anchor his experience at this shindig is his Uncle Luke. He remembers him at various times in his life, making visits occasionally but never much of a talker. But now that he’s older and calmer he finds it refreshing compared to his mother and wonders about the two of them were even raised together.

He’s sitting at the diner waiting for Luke to come downstairs so they can head to the square, rereading a Farewell to Arms when the bell chimes indicating an entrance to the diner. He looks over his shoulder out of curiosity and notices the two women that walk into the diner. The older woman looks to be in her mid to late 30’s with long curly brown hair. She chatters away to a younger girl with short brown hair and a pensive look on her face he immediately takes note of. Both women have pink floral wreathes in their hair to match their dresses, probably to match the renaissance theme of this crazy wedding his mother is throwing. 

“I just think you have to think twice before even getting in the middle of that situation kid. I mean maybe it’s my fault for gossiping about their fights whenever they happen at the inn but gossiping about it in the middle of Doose’s where she can hear you? Not cool. They’re married and it’s his mess now so he has to figure out how to deal with that,” he hears the older woman explain quietly.

“I don’t want to talk about this with you mom,” the younger woman counters.

Jess raises his eyebrows looking at his book. The older woman looks too young to be a mom. Huh.

“Ok ok fine, I’ll leave it alone. Just think about what I said.”

The two women sit next to him at the counter with the younger girl sitting next to him. He can feel her curious eyes on him but doesn’t acknowledge her presence, content to just take notice of her from the corner of his eye for the time being.

She’s pretty, looks to be younger than him for sure. Despite the warmth of the sun these days that has already been darkening his complexion, she seems to be avoiding that entirely with her porcelain skin. Her cheeks have a hint of rosiness to them and he can’t tell if it’s because she’s embarrassed for some reason or if it’s natural. He is tempted to take a full look at her because of her eyes though since even from his limited vision the blueness of them startles his thoughts and-

“Hemingway huh?”

He looks over quickly at the sound of her voice and is faced immediately with the eyes he was curious to get a good look at. And just as he suspected the immense depth of them almost prevent him from responding properly.

Almost.

“Yeah, Hemingway.”

She waits a beat, almost expecting him to continue his thought. When she realizes he’s not going to she grimaces. 

“Oh…well it’s a shame you’re wasting your time.”

He scoffs. “Wasting my time? I’m guessing you’re not a fan of Hemingway?”

“Well if you’re into reading a depressing diatribe that will put you to sleep…”

“Oh I see. And what would you give as a counterpoint to a depressing diatribe? What’s your Hemingway?” he asks with a smile.

“I have to say that The Fountainhead is a weirdly comforting book to me. Always something to come back to when I’m not quite sure what to read next.”

“Oh geeze we clearly have to end this conversation here. Ayn Rand is a political nut,” he groans while closing his book.

“Oh come on, that book taught me all about the art of a well written monologue. If you can like Hemingway I think I can appreciate Rand.”

“Agree to disagree,” Jess concedes.

They stare at each other with smiles on their faces. It’s rare that Jess meets a girl that he’s able to talk about any literature with even if he doesn’t necessarily agree with her choices. It’s a refreshing thought. 

The older woman looks over at them with a curious look on her face. “You’re new,” she notices.

“I’m certainly new to you.”

“Are you here for the wedding?” the younger girl asks.

“Yeah my mom is the bride of this crackfest,” Jess answers.

The older woman’s eyes widen. “You’re Liz’s kid? Oh! You’re Jess!”

The younger woman’s eyes widen as well. “Oh wow! You’re Jess!”

“Well then, apparently I’m not so new to the two of you,” he muses.

“Well after all the gushing Liz has done about you and by extension Luke I feel like there’s a few things I already know but yes you’re still kind of new,” the older woman rambles. “I’m Lorelai by the way, I’ve known your uncle for awhile since I bother him for coffee and sustenance everyday. The Rand fanatic is my daughter Rory.”

Rory gives him a small wave with a smile. “It’s nice to meet you. Luke mentioned awhile ago that you wrote a book actually! I found it in a bookstore near my school. It was good! Cool to put a face to the book.”

Jess ducks his head bashfully, surprised to find that his mother and uncle even talk that much about him.

“It’s really not that good, you’re being too nice,” he murmurs.

“No it was great! The right amount of angst without becoming too overbearing and contrite. Are you writing a sequel?”

“Oh no one needs a sequel. But thanks for asking.”

Just then, Luke comes bounding down the stairs and appears in a sharp looking suit. The only thing he’s ever seen his uncle in despite their infrequent encounters is flannel and a backwards hat. 

Lorelai sits up straighter. “Oh…you look…nice.”

Luke looks up adjusting his tie. “Oh hey, you look…you look beautiful.”

Jess shakes his head and smirks at how smooth this is going. He looks over at Rory who shares a similar look.

There’s a palpable silence that comes over the foursome despite the surrounding noise of the diner that is still operating. Jess decides to do everyone a favor.

“Ok so…I guess we should get going…make sure Liz gets down the aisle I guess?”

Rory nods. “Yeah we should get going, make sure we get good seats!”

Jess, Rory, and Lorelai proceed to get up, gathering their limited belongings and heading towards the entrance with Luke. Luke and Lorelai walk ahead, seeming to engage in short, stinted, and awkward conversation that Jess looks upon with interest. They walk together closely but just far enough that the mood is clearly unsure between them. Rory walks quietly next to him but giggles when she notices the way Jess is looking at the older duo ahead of them.

“This is their first date,” she whispers to him.

“Really?” he says with a raise eyebrow.

“Yeah Luke asked her to go with him and we’re pretty sure it’s a date. They’ve been dancing around this since I was like 10 so it’s kind of a long time coming. I somehow got roped into tagging along since I came back from school this morning.”

Jess laughs at the explanation. “So you’re third wheeling your mother’s first date with my uncle. I’m sorry for you.”

Rory shrugs. “It’s cool. I mean there’s always a ton of people to talk to around here since this is home for me. Plus I figured with it be a renaissance theme there’s totally going to be some great entertainment factor.”

Jess rolls his eyes. “I’ll say. I already had a guy tell me all about how prison totally prepared him for his stint on the circuit last night at the rehearsal dinner.”

Rory giggles. “I’ll make sure to find him for a good talk later then.”

Jess smiles, “I’m sure he’ll show you a good time. We can create a signal in case you need saving.”

“Hemingway could be our safe word, Lord knows I wouldn’t be spouting off about him if I didn’t need help.”

“Yeah I’ll definitely come running when I hear that,” he chuckles as the reach the square. “I have to go over to Ms. Patty’s and meet my mom there. Walking her down the aisle.”

“Oh,” Rory notes disappointed. “Well…I’ll see at the reception I guess?”

He nods. “Yeah I have to save you from potentially dangerous conversations remember?”

The promise to potentially find her again brings the smile back to her face. “Yeah of course. I’ll see you there!”

Rory trails off with her mother and Luke, taking a second look back at Jess as she goes but he is already heading over to Ms. Patty’s.

He walks towards the dance studio and laughs to himself. She’s definitely younger than him but certainly mature if she can bring up Rand and Hemingway in a debate. She’s certainly pretty, not the type he would usually go for but her eyes and natural innocence are not something he has encountered in his life thus far. 

He greets his mother with at least half a smile instead of a grimace, because even though this whole wedding is ridiculous, he at least knows he’ll be in great company to be able to get through the reception.


	2. Chapter 2

One of the few practical things Rory had learned during her freshman year at Yale is that her previous dating experience really left her spoiled. 

She’d only ever had one boyfriend her whole life, and that was Dean. Dean was her first everything: first kiss, first date, first boyfriend, first time having sex, first love. She’d gone through high school never really knowing that she had to work to get a boy’s attention because Dean never wavered. He never strayed and he was always true.

But it became tiring as senior year came around. As she got busier applying for college and the reality of their future loomed over them, the strength of their love sustaining the distance of Stars Hollow and Harvard seemed almost impossible. Yale didn’t seem like a possibility to her then, but even if it was it wouldn’t have made a difference. The distance was never the problem. Dean would have come to see her every weekend if he could. In fact, he probably would have followed her to Boston somehow.

But no, it was never the distance. There was always a barrier between the two of them, an insecurity that grew with every moment in Dean’s heart until it pulled him away. He never truly thought he could fit into her world and keep up with her intelligence. And so soon she avoided him at every turn so that she could get away from fighting with him about the littlest things.

He was the one that finally had the balls to break it off. It wasn’t as painful as the first break up. She cried for half the night, ate some rocky road ice cream and got on with her life. She continued to see him around town, they stayed as friendly as could be expected for the situation. When he met Lindsay she knew she felt strange, as if something was being taken away from her. She always liked Lindsay and she wanted Dean to be happy, so she kept quiet, even when they got engaged and then they got married.

She went to Yale and tried to move on, but dating was harder than she ever thought it was supposed to be. The boys at Yale were certainly smart, but they were not always easy to talk to. One date was disastrous and ended with her hiding in the bathroom talking to her mom on the phone so she could avoid the lack of conversation that was happening at the table. From there the next guy she asked out totally rejected her and her grandma tried to inadvertently set her up with another. She knew she was hitting rock bottom at that point and narrowly escaped that set up by packing up her dorm as fast as she could and heading home sooner than expected.

So it’s no surprise she feels something towards Dean again. As her life at Yale bottomed out from under her and became everything she never expected it to be, Dean stayed the exact way she left him. He was safe and kind and always there when she felt at her lowest throughout the year, even after he married Lindsay and she thought he wouldn’t have any time for her. And the closer they got, the more she saw that he was unhappy with Lindsay. He worked so hard to give this girl everything she wanted and she still complained. But he kept going and Rory would watch sadly as Dean gave up his dreams to make Lindsay’s happen.

It wouldn’t have happened that way if he’d stayed with her she realized too late. He would have gone to college and become something more just like she always encouraged him he would. She knew it was wrong to feel this way, but wasn’t this just how it was supposed to be? It was always supposed to be her and Dean forever, and she knew that when she was 16. He was hers first right? And if they were getting closer while he and Lindsay had so much distance, it couldn’t be so wrong?

These were the thoughts that plagued Rory as she sat next to her mother and Luke and waited for the wedding to begin. She fiddled with her hands and looked around at the decorations and costumes of some of the ushers who were escorting guests to their seats. She looked all the way back to the end of the aisle and noticed Jess standing at the end and waiting patiently for his mother. She seemed to catch him in the middle of staring…at her?

He was definitely gorgeous. While Dean was an All American style of cute, Jess was darker, more of a James Dean style. His hair was gelled and perfectly styled, and somehow she could tell that under his clothes he had a defined but lanky body. She couldn’t stop staring at his crooked smile, pleasantly surprised that it was being directed at her. 

She’d read his book twice. During the second time, she couldn’t help but wonder about what he looked like and what his voice may sound like. His style and his words came through so strong in his writing and the story he crafted. She imagined he was sarcastic, probably abrasive and guarded towards those he didn’t know very well. And even through their limited conversation earlier in the diner she could tell that some of those thoughts were already right. It was rare she got to meet the author of a book she really liked, and she couldn’t tell if her intrigue and desire to talk to Jess more during the reception was about meeting the author or actually meeting a guy she might be able to have a decent conversation with.

Rory gave Jess a bright smile and watched amused as the wedding festivities got underway. An elfish looking girl pranced around throwing flower petals into the crowd and the court jester did an impressive double back flip down the aisle. Liz’s soon to be husband T.J. then made his entrance, strutting down the aisle and casually boasting to the crowd how great his tights were. The grimace Luke made at this was enough to make Lorelai and Rory fall out of their chairs. 

There was nothing to laugh at when Liz appeared in her carriage though. The crowd stood and watched as Jess awkwardly helped his mother down the steps and she latched on to his arms as he walked her down the aisle. Rory could see the pride on Liz’s face when she looked at Jess and whispered something to him, and she could also see the cross between a frown and sheepish look that marked conflict on Jess’s face. From what Rory knew from Luke not everything was always good with those two, but it was at least resolved to a point that Jess said yes to his mother’s request to have her son give her away. 

Jess sat down in front of Rory once his job was and his mother was delivered. She concentrated mostly on the back of Jess’s head and studied the haphazard way his hair was styled in order to keep from bursting into laughter when the officiate came out with his song. She was certainly doing a better job than her mother and Luke.

But she didn’t stop staring at Jess for most of the ceremony, and she didn’t look away when he turned his head slightly towards her and caught her. She couldn’t explain the pull but for the first time in almost a year school was not a constant burden on her mind and neither was Dean and his marriage troubles. It was almost refreshing.

 

After the ceremony Jess and Rory trailed behind Lorelai and Luke to where the reception was mainly being held. The younger duo hung back seeing that Lorelai and Luke had finally hit a groove where their date wasn’t as awkward as it seemed like it was going to be.

“I think my job as a buffer is no longer necessary for tonight,” Rory noted to Jess.

“Well aren’t you glad I’m here to help you out?” Jess mused.

Rory smiled but didn’t answer Jess’s pointed answer and attempt to flirt. “So tell me about Philadelphia. I hear it’s actually kind of a cool city, very up and coming,” she said as they sat down at a table.

“Yeah Philly is very cool. It has a good scene, it’s a lot like New York in how every neighborhood is its own culture but I’m not paying an arm and a leg just to have a roof over my head you know?” 

“And Truncheon? You like working there?”

“A bunch of guys in one room on Locust St working hard to put out books every month? Definitely not what I expected but it’s cool. We have a zine too that keeps everything fresh and try to do open houses that feature a lot of city musicians and artists. It’s cool.”

Rory nodded. “And what about your next book? You have to be writing another one.”

Jess shook his head. “That’s really asking a lot when the first wasn’t that great-“

“Oh stop! It was so great, you have such a unique voice. It’s totally what I imagined it would be when I was reading it. I kept thinking that I could just tell what you would be like just by reading this book and I think I’m right.”

“Oh yeah?” Jess looks at Rory with a smirk. She blushes and looks down sheepishly realizing that her rambling has revealed a lot about her wandering mind. She bites her lip and Jess takes pity on her and changes the subject.

“So you’re in school right?” he asks.

“Yeah…yeah I just finished my freshman year at Yale.”

“Must be hooked on phonics if you got into a place like that. You like it?”

Rory considers her answer for a moment, “It’s amazing. It’s not where I expected to end up since I always wanted to go to Harvard but it’s been an amazing year.”

Jess takes a long look at Rory and raises his eyebrow. “You sure?”

“Why would you doubt that?”

“Because something about the way you answered is telling me it wasn’t all amazing.”

She frowned and looked away at him, blushing that he could see right through her façade. She’d gotten good at playing this game with everyone else in her life, acting as if everything at Yale was as perfect as it was when she was at Chilton. It wasn’t all lies, she did love her time at Yale. But it was different. It was hard. At Chilton her hard worked paid off and she was the best at what she did but now she worked just as hard and sometimes that didn’t happen. She got D’s on papers and was told she had to drop classes and that her pieces wouldn’t make it into the paper. 

Less than a day with this guy and he could see right through it all.

Before she could answer Jess the crowd around them erupted in applause as Kirk announced the first dance for Liz and TJ. The two watched as the slow melodic tune led the newly married couple around the dance floor. After a minute Kirk made another announcement that other couples were encouraged to join the newlyweds. Rory saw Luke suavely lead her mother towards the dance floor and lead her in waltz that sparked surprised looks on both Gilmore girls’ faces. 

“Woah…Luke can waltz” Rory mused, totally forgetting about the previous conversation.

Jess nodded along dumbfounded also forgetting about the pointed observation he’d made about his companion. “Who would have thought?”

Rory turned to Jess. “Think you’re brave enough to show him up?”

Jess scoffed. “You don’t want to dance with me, you’re only doing this to avoid talking about school.”

“Well maybe that’s what I’m doing but I also do want to dance with you. Maybe I’ll even give Hemingway a try again?”

He shook his head laughing to himself, “Whatever you don’t have to do that. I’ll dance with you, Lord knows Liz will make me do it at some point.”

He stood up quickly and took Rory’s hand, leading her towards the dance floor. He pulled her into his arms, swiftly wrapping one arm around her waist and holding her hand with another. 

He wasn’t a dancer, but he knew what it took to charm a woman. Rory was still holding his interest and a part of him knew where he wanted this night to end. She seemed to need a little fun since she obviously had some unsaid issues going on with school, but she was overall interesting and bright. The longer he stared at the blueness of her eyes paired with her porcelain skin the more he forgot about his notions of having a “type”. His hand around his waist could feel the subtle curves that her dress hid and the back of his mind went to another place, one where he got to discover how red her skin could get as he made indents along her stomach with his fingertips, sucked on her collarbone that peaked from her dress. He didn’t know if she was a virgin, but he did understand that he was older than her and that he would probably have to tread carefully.

Rory leaned her forehead against Jess’s shoulder, a little breathless at the quick and confident way he took her into his arms. He smelled faintly of tobacco but also sandalwood. The two danced in silence, lost in their thoughts about each other with Jess pulling Rory’s body closer to his, enough so that his body warmth was feeling like second skin to her. 

Rory wasn’t like this. She’d never met a guy that she had felt so instantly connected to that she would even consider pulling him away from the reception and finding a quiet place to be alone with him. She’d only ever been with Dean and it was nice, but she’d never considered that she would want to be with someone else. She raised her head up from Jess’s shoulder and saw that he was once again staring at her. At other points throughout the day his stare had been curious, and it still was, but his eyes had darkened and she didn’t think she could attribute it to being nighttime. 

She imagined that because Jess was older he certainly knew what he was doing. He was gorgeous and probably attracted girls of the same caliber down in Philadelphia. Rory always considered herself to be classic, never sexy or gorgeous but just…pretty. But the way he stared at her told her he was seeing something she wasn’t. She wanted to find out.  
“So, during this ‘amazing’ year you’ve had at Yale, did you happen to find a boyfriend while you were there,” Jess casually asked. It was an important question. He was never about being with a girl that was taken.

Rory immediately thought of Dean and felt a pang of guilt. All day she had forgotten about the messy situation she was getting herself into. It was ironic that just as she first laid eyes on Jess in the afternoon her mother was trying to subtly talk some sense into her. She didn’t know where things would go with Dean. She was sure he was close to leaving Lindsay and it made sense for them to try and pick up where they left off in high school. But Jess didn’t know any of this. Jess didn’t even live here. He was a completely separate entity from the complicated web Rory had spun between school and Dean.

“No, no boyfriend to speak of,” she told him, making a decision in her mind.

“Huh.” Jess smiled.

The two continued to dance, not noticing the song had changed all the while changing their rhythm to the new tune.

“You know, I didn’t get much of a chance to see much of the town when I got here,” Jess mused. 

Rory raised an eyebrow. “Oh really? That’s too bad, it’s really a beautiful town.”

“Well maybe there’s still time, especially since you seem pretty capable of being a good tour guide.”

“I think I know some spots you might like. It’s especially quiet this time of night with a town function going on. Definitely could be a more intimate tour.”

Jess grins and lets go of Rory regretfully but keeps her hand firmly in his. “Sounds like a good plan then. Shall we bail?”

Rory looks around for a moment, eyes landing on her mother. She and Luke are in their own world eating turkey legs and laughing. She probably won’t notice Rory is gone, thinking she’s gone home or found a corner to read in. As cool as her mother is, she doubts she’d want to see her only daughter walk off with some older guy to possibly hook up with him.

Rory turns back to Jess with a determinedly confident smile on her face. 

“Yes.”

**Notes for the Chapter:**

> Going to be honest that I didn't initially plan on these two hooking up so soon but something about them just makes me want to pull them together sooner. Please leave your thoughts and feedback!!


	3. Chapter 3

Jess has never been shy about sex.

It's just a given. He lost his virginity when he was 15 in the back of a club that he wasn't supposed to be in with this girl Sasha that was a senior in high school showing interest in him for a couple weeks. That was the first and last time he was ever awkward and shy when he had sex. He figured that it felt good…really good. And if he wanted to get the most of out it, being shy about the situation wasn't going to get him anywhere.

He's not an asshole and he never tries to force a woman to do anything she doesn't want to do but he definitely doesn't think not asking for what he wants during sex is a good idea either. What's the point? He could be doing other things. He could be going over the next great manuscript for Truncheon instead of trying to be with a girl who didn't want to make it truly mutually beneficial.

He had his doubts as he walked hand in hand with Rory through the quiet town. She had led him over to a bridge where she pointed out that this was her favorite place to come and read. He could see why. It was quiet and when the moonlight hit the lake just right it reflected a spotlight that couldn't be created by street lamps. He could imagine kissing her creamy skin all over, slipping off the straps of her dress down her shoulders and exploring the indent her collarbone made as he laid her down on the hard wood of that bridge.

It was a nice thought but he was not willing to get splinters in places it shouldn't be.

She had looked at him curiously as they stood at the edge of the bridge, edging closer to him, prompting him to kiss her with those eyes. But he knew that once he kissed her he wouldn't be able to stop.

He gave her a smirk and asked if they could keep going.

They walked for another 10 minutes, through some lush grass and fairly treacherous bushes. They laughed together as they almost tripped over twigs, never letting go of each other's hands. When they emerged they came upon a clearing with a lake even bigger than the one by the bridge. He could see a swan in the distance on one side, and the remnants of what looked like an old building beyond the lake.

"This used to be the old Independence Inn that my mom managed. It burned down in a fire almost a year ago and closed down but at least that meant she could start her dream of opening her own inn. That's opening in a few weeks. But this is special. You see that little shed over there? That was my first home. When my mom came here with me when I was about a year old the owner of the inn let us stay here and we made it into a little house. It still gets used sometimes by people," Rory explains pointing out the small shed in the distance by the edge of the lake.

Jess looks around, actually impressed by all the natural beauty he's encountered in this town, his companion not included. "Huh."

Rory laughs at his simple answer. "Come on, let's sit."

She leads him towards the lake, taking a seat on the grass and looks at him expectantly when he doesn't immediately sit down with her. He takes a moment to look around and finds that the moon still hits this lake just the way he wanted to. Funny how that works.

Jess sits down next to Rory and wraps his arm around her waist to bring her closer to his side. He leans down towards her ear. "You know I was a little reluctant to come to this whole shindig but I'm glad I let my mom and Luke talk me into it. I mean you're a little crazy for being into Ayn Rand and all but you're young. You've got time."

Rory scoffs with an amused smile on her face, "Oh really? So I like Rand because I'm young? You know there's a lot I could say about you liking Hemingway because you're old and boring. You're in your 20's right? That's getting up there-"

Rory is cut off by Jess pressing his lips to hers, sucking in the words that had yet to come out of her mouth. She inhales sharply before opening her mouth, letting Jess take the lead to slip his tongue in her mouth and explore the crevices. Every nerve in her body lights up like a Christmas tree and it take her brain a few seconds to catch up with her body. She knew this is where it was leading, but she couldn't help but be surprised at how different it was. The only man she'd ever kissed was Dean and while there was a rush that came with your first love, it was never quite like this. Rory wrapped her arm around Jess's neck, reaching into his hair to push him closer to her.

Jess brought his other hand to Rory's face, taking gentle hold of her cheek to tilt her head back. His kisses became softer, sipping at her lips and stroking his hand from her cheek down to her neck. Rory could feel the heat his body emitted through his clothes and the warmth it created in her own spurred her to lessen the distance between them. Without disconnecting, she straddled herself in Jess's lap. He moaned in surprise at her forwardness and how good it felt for her center to come in contact with his.

Jess breaks away from their kiss and trails a series of open-mouthed kisses down Rory's throat, sucking along the apex of where her neck and collarbone meet. Rory arches her back in desire for more, unable to control her body and its responses. She grasps Jess's shoulder and threads her fingers in his hair, urging him to keep going.

"That feels really good," she panted.

"Yeah? You want me to keep going?" he asked against her shoulder.

She couldn't answer, as his hands were now all over her body and rendering her speechless. She nodded.

"Good. I want you to tell me what you want though. And I'll tell you what I want ok?"

Rory moaned at the contact Jess was making with her left breast, kneading and flicking her erect nipple that was making herself visible through her dress. "I don't…I don't know what I want. I've never done this…"

Jess's hand stilled. "Are you a virgin?"

She shook her head vigorously, "No! No I just…I've only been with one guy. I've never done this with-"

"Someone you don't know," Jess finishes. He gets it now. He figured she wasn't that experienced, but to hear her be so nervous made him pause. He'd have to change his approach. Sure he always valued being able to tell his partner his sexual desires and vice versa, but he wasn't sure Rory was quite equipped for his style at this point.

"Ok. Well I'm not going to hurt you, and I need you to trust me. Trust me that I'll give you what you want. That I want to make you feel good," he tells her, catching her eyes.

Rory stroked his hair back smiling. She pressed a series of kisses to his cheek confirming her acquiescence.

"So tell me what you want," he said with a smirk.

"Well what can you do?" she countered.

He brought his hand slowly up her thigh, reaching under her dress that had bunched up in her lap to grasp her ass. He pushed her against his groin, thrusting into her so that she could feel the full weight of his cock hidden beneath his dark jeans. She gasped and threw her head back, undulating her hips against hers. She'd felt this ache within her once Jess kissed her and it burned as their encounter intensified. The ache felt good and the way Jess thrust against her created a spread throughout her core.

Jess laid down on the grass and pushed Rory up so that their cores were still aligned with each other. He grasped her hip with one hand, moving her back and forth and let the friction their bodies sparked lead her towards more pleasure. He took his other hand up her skirt, pushing her skimpy bikini panties out of the way to stroke against her clit.

"Oh god," she exclaimed breathlessly.

Jess pushed his thumb against her clit, stroking in circles and in tandem with the strokes of their hips. Rory panted and moaned, leaning her hands onto Jess's chest to stabilize herself. She took control of her own movements, not needing Jess's hand to guide her any longer and freeing him up to explore other parts of Rory's body. He eased down the thin straps of her dress to reveal her breasts. Jess groaned at how her milky skin reflected in the moonlight, her nipples dusky and erect.

"God you're gorgeous," he whispered. She didn't seem to hear him, lost in her own fog and pushing against his hand harder. She wanted more and she was almost there but she needed something.

"More," she moaned. "God, I'm almost there. Please don't stop."

Jess pushed against her clit harder but was constrained at their position. He could tell she was close, she just needed that last bit. He knew how to get her there, but he wasn't sure she would go for it, if her inexperience gave any indication.

He did tell her to trust him though.

He lifted his hips up and wrapped his arm around her to secure her while rolling over so that she was under him. His hand that was pleasuring her now fully removed her panties to get rid of the obstacles that they presented. He inserted two fingers in her core easily. She was so wet that he felt like he was gliding against her walls. Her mouth opened wide as if she was screaming but no sound came along with it. Jess moves his fingers in and out with the motion of a come hither, hitting the right spot every time. Rory closes her eyes, overwhelmed and almost out of her body. She reaches and grasps the grass underneath her. It almost grounds her to the moment.

"You know what I want once you cum Rory?" Jess asks. Rory opens her eyes and looks into his. They had a light brown touch during the day but right now in this moment they are almost black and she can't look away. He leans down and presses a quick kiss to her lips, and whispers in her ear, "I want to taste you and make you scream because I bet the one guy you've been with didn't do that for you. I want to lick you until you can't see straight and then once I've done that I want to fuck you. I want you back on top of me because you can't get enough and you want your body to take control. You looked so gorgeous when you were top of me earlier and I want to see it again."

Rory couldn't take it, the combination of his words and the way he was making her body feel brought her to the edge. She bucked against him, her core tightening around his fingers, locking them in. Jess watched in amazement as her face and neck turned a lovely shade of pink as she gasped and came. She wanted that too. She didn't know that's what she wanted when she started this with him, didn't know this is what sex could be like. She felt so out of control and even though she had been pretty much all of her freshman year of college, she actually liked this. She brought his head down to hers as she came down from her orgasm, kissing him passionately. They stayed like that for a few minutes, holding each other close. When she finally broke the kiss she brought their foreheads together, breathing deeply into each other.

"Yes," she breathed. "I want that too."

**********************************************

The two laid side by side on the grass having put their clothes back to rightness. Rory's head leaned on Jess's shoulder and his arm was wrapped around her shoulder. Their eyes were closed, but they weren't sleeping, just merely listening to the sounds of the lake and the surrounding birds still awake with them.

Rory opened her eyes finally after another 5 minutes, taking note that it must be close to midnight at this point and she should probably be getting home. She turned her head towards Jess. "We should go. I have to get home."

Together they walked back the way they came, hand in hand again and not saying a word, lost in their own thoughts. When they got close to the Gilmore house they saw Lorelai and Luke standing in front of their porch in the distance. They were laughing together, almost wanting to get closer and make contact but still not over the awkwardness that this was the end of their first date. Upon hearing a branch that broke under Rory's foot, the older pair turned their attention to the younger duo coming towards them. Both looked confused at Rory and Jess, noticing how disheveled their hair looked and the grass stains on Rory's dress and Jess's shirt. Lorelai's eyes widened when she realized just where her daughter had disappeared.

"Oh," Lorelai whispered. "Looks like you two got to know each other better."

"Hey mom," Rory responded uncertainly. "I was just showing Jess around town and we just ended up at the old inn and you know how the grass gets."

Lorelai pursed her lips and crossed her arms. "I see. Well it's getting late so say goodnight to Jess huh?"

Rory turned to Jess sheepishly and whispered her goodbye. She turned to walk towards the house when he took her arm and pulled her back towards him, kissing her quickly on the cheek.

"I'm not leaving until tomorrow morning, have breakfast with me at the diner ok?" he whispered. She grinned at him and nodded before hurrying back into her house, past her mother and Luke and avoiding their gaze.

Jess watched after her until she walked into the house, not turning his attention towards Lorelai's judging gaze and Luke's curious one. When the door closed after her he turned away back towards the diner with a smile on his face.

Best wedding ever.

**Notes for the Chapter:**

> I always have this plan when I start the chapter and then by the time I get to the end I'm at a completely different place. It's what these two do to me!


	4. Chapter 4

Rory woke up the next morning and listened closely for any sign of movement in her house.

When she scurried inside her house after her illicit, out of character, very public sexual encounter with Jess, she immediately retreated to her room and locked the door. She threw her clothes in her hamper and put on her pajamas with the cupcakes and burrowed under the covers in the dark. When her mother knocked on the door 15 minutes later she said nothing, pretending that sleep had come over her with no time to argue with her mom who obviously had an idea about what she had just done. 

She didn’t need to ruin this for her. Rory could do that all by herself. 

It took her another hour to get to sleep, despite feeling exhausted and a little sore from her activities. She blushed thinking about how she got this way. She didn’t know what had come over her hours before. Earlier in the day she was complaining about Lindsey mistreating Dean, her first love but by the end of the day she’s having sex by the lake with Luke’s nephew Jess who she had just met?

She wracked her brain for some sort of sense of what she had been thinking to do something so stupid. Would it even count as a one night stand if she was going to see him tomorrow? Did she want to see him tomorrow? She was going to have to. At least they used protection. At least he was incredibly hot and intelligent. She really could have done worse for herself. And at least he knew what he was doing.

At that thought, Rory blushed even harder. 

She turned onto her side facing her window and looked out to see that the stars were still shining a bit in the sky. They somehow looked duller than they did earlier in the night when she was with Jess. If there’s one thing she won’t forget from tonight, it’ll be the way the stars morphed into different colors as she came the second time that night when Jess went down on her. The way her five senses had been overhauled with the silkiness of his hair through her fingertips, the sound of her own moans ringing in her ears, the smell of the grass, the taste of herself on her tongue from Jess kissing her after taking his first taste of her, and the sight of the stars becoming like the rainbow.

Thinking of that moment brought her back down from her anxiety. She had never been able to achieve those heights by herself or with Dean before. She had read about it in books as if it was the mythical peak of romance and adulthood. She’d studied its clinical aspects in her health classes. But she’d never had that before. She’d never been so bare in front of another person, laid out with the most vulnerable parts of her ready for someone else to take from. It had been scary with Dean but also logical. It was clearly the next step in their relationship and she’d taken all the necessary steps to make it happen. She told her mom and she took her to doctor so she could get on the pill. She and Dean had talked about the pros and cons of taking that step and she encouraged him to get condoms just in case. Silently she thought that this step would bring something back to their relationship that was fundamentally missing. And it was fine when it happened-awkward but ultimately romantic. The handful of times they did it before they broke up got better as they learned more about each other’s bodies, but Dean was never able to make Rory go quite over the edge.

Not that she ever let him know that.

He handled her like a doll and while she appreciated the love and care that it obviously showed, it wasn’t enough. She hated to compare the two but with Jess he pushed her without throwing her over the cliff completely. He didn’t know what she wanted, because he didn’t know her, but he asked her and wouldn’t stop until she got it. Even when he was getting all his desires met in their encounter he still demanded, “Tell me its good, make sure it’s good enough.” He was relentless until she was satisfied. And she was…three times.

Rory had always been naturally curious about most things, wanting to learn more about something until she understood how it worked. She hadn’t been that way when it came to sex with Dean, but now with Jess she couldn’t stop playing everything in her head on a loop. How had he made her feel so out of control of her own body yet so in control at the same time? She’d never had someone go down on her before and she certainly had never had sex while on top. And while she felt scared and silly that she even put herself in this situation, she was also curious about what else Jess could make her feel if tonight was any indication.

When she finally fell asleep, she reimagined the moments after they both came, spent with Rory slumping down onto Jess’s bare chest. He’d brought his hands up to stroke her bare back and placed a kiss on her forehead. She panted heavily, trying to catch her breath and make her muscles and brain align with each other once again so she could move. She lifted up her head to look at Jess, almost afraid at what she would find-that he would immediately push her off him, having gotten what he wanted and making her feel like a fool as he walked away. She found a soft look on his face, one that she hadn’t seen from him all day. 

“Good?” he simply asked. 

She looked back at him in wonder. “Yeah…good.”

He nodded and brought her face to his to join her lips in a slow kiss, memorizing and savoring the way their lips felt together. She broke away and smiled against his cheek, wanting to rest there for a moment before reality set in again.

She slept well the rest of the night.

When she listened for any sign of her mother in the kitchen or living room, she only heard silence and thought that it was finally safe to make an appearance. She wasn’t sure what time Jess was leaving this morning, but she wanted to get to the diner with enough time to say goodbye. When she came into the kitchen she saw a note on the table from her mother letting her know that she had to get the inn to look over a few things but she would meet her at the diner in a hour or so. 

She also made a snide remark about not getting in Jess’s pants again while she was gone but she was just going to ignore that. 

She showered and got dressed quickly in a simple pair of jeans and light sweater. She headed to the diner in earnest as it was already 10 in the morning and she at least wanted to get to the diner and see Jess before her mother got there to ruin it with her judgment. 

When she entered the diner, the familiar bell rang and she was faced with the usual busy morning rush. Babette and Morey were in one corner having their usual breakfast with Kirk at the counter probably asking Luke ridiculous questions. She looked around and found Jess behind the counter, leaning against the other side engrossed in his book. She walked up to the counter and waited for him to notice her, but before that happened Luke came from the kitchen.

“Rory!” he exclaimed surprised. “You’re here!”

Luke looked alarmed, as if the last thing he expected to see was her. Jess looked up from his book at Luke’s proclamation, and his mouth quirked up to a crooked smile when he saw Rory there. Rory waved sheepishly at the two men. 

“Hey Luke. Could I get some coffee and pancakes…actually eggs and bacon if Caesar is making the pancakes,” she ordered. 

“Oh…you’re not going to wait for your mom?” Luke asked confused.

“She’s having breakfast with me actually,” Jess answered for her. “She promised we’d talk about the books she read for her philosophy class she took this semester.” 

Luke looked between the two of them, Rory’s face staying neutral so that it wouldn’t betray the obvious lie Jess just told. 

“Ok…what do you want then?”

“Eggs and sausage. I’ll get out of your hair once we have breakfast.”

Luke nodded and looked between his nephew and Rory again before muttering that he’d be back before going back to the kitchen. 

Jess came around from the counter to sit down next to Rory. 

“We meet again,” he said as he sits down. 

“I suppose we do,” she responds with a smile.

The two sat for awhile until their food came, actually talking about the philosophy class that Rory took this spring semester. They compared notes on some of Nietzsche’s writings which Rory was surprised to hear that Jess actually liked. She was amused by his affinity for Camus as well.

“It was the first book we had to read for the class but I already read it a couple times in high school. It actually makes sense that you would like it,” she mused.

“Yeah I mean existentialism isn’t the end all be all for me but I get it you know. In the end we are who are once we cut out the bullshit labels that other people put on us. I wouldn’t have written my book if I’d let that kind of thing hold me back you know? Freedom is pretty essential.”

Rory looked at him thoughtfully over her pancakes, his words striking a cord with her. “Yeah I think I do get that…sort of.”

Jess tilted his head recognizing that the wheels in her brain were turning. “So what did you not like about it?”

“It’s not that I didn’t like Camus or Nietzsche, it’s just that it was almost too cynical for me. We don’t live in a vacuum you know? There are people other than ourselves that we have to consider when we make decisions.”

“Were you thinking about anyone else last night?”

“No…no of course not.”

“Well then you made that choice completely independent of outside influence. And if you’d actually considered what other people thought, like your mom who did not look happy to see us last night, you wouldn’t have done it. And you would have missed out on a good night. It was a good night right?” he asked cockily.

Rory blushed at the mention. “You don’t need me to tell you it was a good night.”

“But it was, and now we’re sitting here waxing poetic over existentialism.”

The two sat quietly for a moment, taking a bite of their food.

“Hey,” Jess broke the silence, “I hope you don’t let anyone else ruin that for you…last night I mean. I can tell you’re pretty close with your mom and all but in the end that was about you and that was about me. And I had a pretty good time and I’m guessing so did you. That’s all that matters. I hope you don’t let someone else make meaning of that for you.”

Rory looked at him surprised. “Um…thanks? I mean my mom is pretty great, she’s my best friend but I guess I am still her daughter in the end so I can’t get away her judgment on some things.”

Jess merely nods and takes one last bite of his breakfast. “I get that.”

He throws down his napkin and takes a look at his watch. “I have to go unfortunately. Shitty drive back and I have a meeting with a new author tomorrow morning.”

Rory looked at her pancakes disappointed. “Oh.”

“Yeah…walk me to my car?”

Rory nodded and took a one last bite of her own breakfast while Jess got up to go get his bag from behind the curtain. 

“Luke!” she heard him call out from behind the curtain. “I’m out!”

Luke came back from the behind the kitchen looking around. “Already?”

Jess appeared again from behind the curtain, this time with a small duffel bag. “Yeah it’s a bit of a drive back to Philly. Here’s some cash for the breakfast, Rory’s too.”

“Ah no,” Luke waved off. “Consider this a thank you for coming up here. I know you and your mom it’s always…weird so I appreciate you making her happy this weekend. Don’t be a stranger kid.”

Jess smiled wryly. “Thanks Uncle Luke. It was good to see you.”

The two shook hands and Jess quickly made his way around the counter back to Rory. 

“You ready?” he asked.

She nodded and followed him out, ignoring Luke’s curious gaze at the two of them.

The two walked out into the bright sunny day of Stars Hollow and Jess lead them to his car that was parked right outside of the high school. 

“So…it’s been fun I guess?” Rory questioned. She wasn’t sure what to say now. Through all this time since last night and this morning, Rory had ignored the very clear barrier that Jess lived in a completely different state hours away. She had sex with a guy she didn’t know and now he was leaving. 

“I guess? I’m hurt,” Jess laughed. He turned to look at Rory who was biting her lip in uncertainty. His look softened and he placed his duffel bag down and took his phone out of his pocket. 

“I don’t use this thing very often since I was kind of forced into it by the guys at Truncheon but…you got a number Rory?”

Her eyes widened, “You want my number?”

Jess shrugged. “We could talk sometime. You could tell me about giving Hemingway a second chance.”

Rory blushed and gave Jess her number. He punched the numbers in and called so that Rory would have his number as well. 

“And see now you have mine.”

Rory nodded and wringed her hands together, still not knowing what to do with herself. Jess bent his head a little to catch her attention. “Hey you should come visit Philly sometime…I think you’d like it.”

“Yeah? Only if you take me to get a cheesesteak. I hear those are pretty good.”

Jess rolls his eyes. “I’ve never had one, it’s a shitty tourist thing but I guess we could try.”

The two laughed and continued to smile into each other eyes, neither wanting to actually say goodbye. 

Jess’s eyes shifted around to look at their surroundings. “So here’s the thing, I would kiss you goodbye but I see your mom looking at us over there from Luke’s and I don’t want to put you in deeper shit. So I will just you with this,” he explained as he pulled a book from his back pocket. It was his copy of Hemingway that Rory had first spotted him with yesterday. 

“Why would you give me this?” Rory asked confused. 

“Just look inside.”

She followed instructions and opened the book to see small writing around the margins, writings that seemed to indicate Jess’s thoughts and musings about the chapters. 

“You’ve really read this before,” she said amused.

Jess nodded. “Let me know what you think.”

He turned away and loaded his duffel bag in the bag of his car. Rory watched as he opened the door to the front seat, but before he sat down he looked back at her with a smile. “It was great to meet you Rory,” he said with a wave.

Rory waved back shyly. “Yeah you too.”

He got in the car and drove off leaving Rory with his book clutched to her chest. She watched his car get further away before she turned back to the diner and saw her mother watching her from a table at the window. 

She remembered what Jess had told her. She had a choice here to let Lorelai make her feel guilty about what happened last night, to let her ruin something that had if she was going to be honest shook her to the core and woken up her spirit. Her mother would probably not quite understand that, expecting Rory to go about things the way she always had. Girl meets boy, girl starts to date boy, boy gains mother’s approval, and then girl and boy have sex. But Rory had a choice to not let that define her for once and as she walked back to the diner she was going to take it seriously.

She walked into the diner and sat purposefully across from Lorelai who was sipping her coffee and looking expectantly at her daughter.

“Did you eat already?” Lorelai asked.

Rory nodded. “I had some breakfast with Jess before he left.”

“Ah…that was nice of him. Most one night stands don’t do that sort of thing.”

Rory just looked at Lorelai. “Mom you’re my best friend so just…say what you’re thinking ok?”

Lorelai put down her coffee cup. “You sure you want me to do that? Because I’ll be playing more of a mom card here.”

Rory shrugged.

“Ok then. That was a dumb move kid. Walking off with some guy you don’t know and have never met before, having sex with him in what sounds like to be a very public place? What if he had hurt you? What if he had some crazy disease that he just passed on to you?”

“We used protection mom, you taught me well in that regard,” Rory reasons. 

“But still kid. What were you thinking?”

“I was thinking that there was this incredibly attractive guy who was intelligent and funny and he was interested in me and it just happened ok?”

“So what happens now? He goes back to Philadelphia and what now? Are you in a relationship?”

“No of course not.”

“So will he come back here and visit you?”

“We didn’t talk about that.”

“Yeah I bet there was no time for that. So he got what wanted and now he’s gone back to his life where he’s probably got other girls all lined up to greet him back.”

“You don’t know that! You don’t know anything about him!”

“And neither do you!”

“Why is that such a problem? I’m an adult now. I can make these decisions on my own. You’re just mad because I didn’t consult you first, that I didn’t ask you permission and get your approval. Well too bad. Maybe I won’t end up marrying him let alone dating him but that doesn’t mean it was wrong! He gave me his number and I have his and maybe we’ll talk sometimes but you don’t get to judge this just because I didn’t do it the way you think I should have.”

“It’s not that Rory…this just wasn’t you!”

“What because it was spontaneous and exciting?”

“No because it was reckless and stupid. You’re not stupid.”

“Sometimes I am mom,” Rory exploded. “You know I had to drop a class this semester because I was failing, I’m not this special snowflake that you’ve always proclaimed I am. I don’t do everything perfectly. I’ve been trying really hard but I still have been failing. I get D’s on papers, I have to drop classes, I can’t date right at Yale. Last night was the first time in awhile that I have felt free from all of that and you’re ruining it for me.”

Lorelai blinked surprised. “Rory I-“

“No,” she said firmly. “Please stop. Don’t ruin this ok? Just forget it happened.”

The two looked defiantly at each other until Lorelai finally relented. “Fine…ok. As long as you were safe.”

“I was,” Rory confirms. 

Lorelai takes a sip of her coffee and gets up. “Look I have to go back to the inn but…movie night tonight? Celebrate you being back? You get to pick.” Her voice become more upbeat at she tries to bring a regular smile back to her daughter’s face.

Rory relents and gives her a small one. “Sure…how about you pick the movies and I’ll pick the food?”

“It’s a deal.” Lorelai gives Rory a quick kiss and heads out the door. 

Rory stays in her seat and plays with the pages of Jess’s book. She considers going down to the bridge to start reading it. Or maybe the old inn. It’s a nice day for it.


	5. Chapter 5

**Notes for the Chapter:**

> Happy holidays all! I seriously expected to have more time to put out some more chapters this week since I have a nice break from work but laziness takes over. I’ve been thinking about this story a lot though and I’m excited with where it’s going. I hope you are too after this chapter! It may seem a little nutty in the middle but trust and believe I’m a die hard Literati until the end.

In the following weeks after Liz’s wedding, life seemed to go back to normal for Rory and Lorelai. The incident with Jess was ignored for the most part by Lorelai as she took Rory’s requests and pleading to drop it to heart. She also was far too busy finishing up the last minute preparation for the inn before it opened. Since Rory had so much free time on her hands, she enlisted her help to make everything happen. The Gilmore girls spent their days at the inn and their nights juggling fun movie nights and doing preparations that could be done at home. 

Rory heard from Jess via text a few times. They held pretty superficial conversations at least once a day, mostly about the books they were reading. One night Jess live texted her through a poet at Truncheon that did a hour of haikus for their open mic night. It was just as torturous for her as him by the things he was texting but the smile it brought to her face when he thanked her for putting up with the texts and being a safe harbor for the night was unmatched.

She’d only managed to read his copy of ‘The Sun Also Rises’ once in the past few weeks, because even if she did enjoy his musings in the margins it was not going to make her like Hemingway. She loved reading his thoughts more than actually reading the novel. It gave her further perspective into how his mind worked and she almost understood how Hemingway and Jess were a perfect match for each other even if she didn’t find she could appreciate him that much. She could feel his passion and how thoughtful he was about not thinking about Brett immediately as a villain. It spoke volumes to her and she immediately wanted to read The Subsect again after to compare the two. She could see the influences of Hemingway and Kerouac within the story now that she was looking for them. She texted him and told him that she’d read his novel again and wondered how he’d managed to create a perfect mix of those two authors as an influence without it becoming incredibly phony. He told her they’d have to discuss the next time they saw each other.

It was the day of the test run at the inn where all of their friends in Stars Hollow would come stay as guests for a night in order for the staff to work out the kinks in their operation. Rory was going around filling the flowers and dodging the construction crew that was going around and putting in the doors for all the rooms. It was a completely last minute endeavor but that was life for Lorelai Gilmore. Rory scurried through the dining room into one of the hallways to get back to the front desk when she found herself blocked by Dean carrying a door. There wasn’t a logical way to get by him in the hallway and they both laughed nervously as he put down the door and laid it against the wall so that Rory could get through.

“Hey!” they both exclaimed at the same time. Nervous laughter erupted between the two of them again. 

“I haven’t seen you around town lately,” Rory noted.

“Yeah I’ve been pretty busy, with finishing things around here and being at Doose’s. Lindsay has also been insisting on making dinner a lot lately, her mom has been teaching her how to cook.”

“Oh…that sounds nice.”

“Yeah,” he shrugs. “She also…she told me about what you said at Doose’s the other day and she definitely wasn’t happy about it. She figured out that we’ve been talking and that I’ve been telling you things…she doesn’t want me to really talk to you anymore.”

“Oh,” Rory responded despondently. She couldn’t really be surprised by that turn of events. If she were in Lindsay’s position she would feel the same way. That didn’t mean that a feeling of ownership didn’t still lie in her, bubbling up to the surface as her conversation with Dean progressed. Dean was her friend, he was her first love and Lindsay didn’t get to dictate who he was friends with, how much he worked, or if he went to school. 

“I’m sorry I’ve been causing so much trouble with the two of you,” Rory said diplomatically. As much as she tried, her mother’s voice echoed in her mind along with her other thoughts, reminding her that being in the middle of this situation was a bad idea. Jess had given her a reprieve of sorts, but she couldn’t avoid the Dean situation forever. 

“No it’s not your fault. You and I have always been close and I don’t want to lose that,” Dean whispered while coming closer to her. The hallway they were in was not narrow but with the addition of the door he was supposed to be moving it was like they were in their own little private corner.

“Rory,” Dean sighed, “it’s just that things that Lindsay are not totally working you know. We’re trying, we’ve really been trying but it feels like something has been missing, especially on my part.” At this point, Dean had boxed her in between him and the door, leaning against the wall with his hand. 

Rory looked down and twiddled her hands nervously. “I see. And what do you think has been missing?” Somewhere in her head she knew where this was heading, but she didn’t see a way out of it. 

“I’m just…I’m not happy. I remember when I was with you…I was really happy then.”

“Dean-“

“Rory I promise you it’s over with me and Lindsay. I rushed into that when I really just wanted to get over you but it was such a mistake.”

Rory’s face softened at his admission. “Dean I don’t know what to say?”

Dean cupped her cheek with his hand, tilting her head up in perfect position to give her a kiss, a move she was incredibly familiar with. She knew what was coming but she felt immobile to stop what was happening, lost in thoughts of Lindsay, how comforting it always was to be with Dean, and of course what about Jess?

“Say you want to be with me too,” he pleaded.

Rory simply looked at him and didn’t say anything, unable to put into words what she was feeling. Dean took her silence as acceptance and leaned in to kiss her softly. Rory leaned in to it, remembering how soft Dean’s kisses always were. It started off as it always did, soft and tender, tentative until he could gauge her mood. She opened her mouth reflexively and Dean tongue entered her mouth, entwining with hers. His other hand went to her waist and leaned them both against the wall so that he surrounded her. His kiss became more aggressive and Rory struggled to keep up with the way his mouth moved against hers, stealing her breath away.

She couldn’t help but think that Dean’s hands and kisses always felt pleasant and comforting but that feeling was foreign to her in this moment. She wanted more, and even if Dean seemed to be pushing it wasn’t enough. 

Dean wasn’t enough.

Rory’s limp arms at her side took action at this point, gently pushing Dean away enough to break their kiss. “Dean wait.”

Dean pulled away enough to look at Rory with a confused expression. “I’m sorry, I thought…”

Of course the conversation was broken because at that moment Lorelai came upon them in the hallway. 

“Oh!” she jumped startled. “Uhhh…”

“Mom!” Rory yelped, pushing Dean far away from her so that they were no longer touching. “Dean was just going to attach this door upstairs,” she rambled.

Lorelai crossed her arms and looked at the two of them with a quiet anger that Rory had rarely seen on her mother in her 19 years of existence. Dean seemed to almost shrink under her gaze and muttered an apology before scrambling to gather his assigned door and get by them with it. 

As he left, Lorelai continued to look at Rory while she crossed her own arms and avoided her mother’s gaze. 

“Listen I don’t know what you think you’re doing Rory,” Lorelai started, “But this is incredibly stupid and you’re not a stupid kid. I don’t play the mom card very often but I’m going to do it now. You need to stay away from Dean. He’s married! I’m trying to open an inn and I have you making out with your married ex-boyfriend!”

Rory’s eyes filled with tears because for all her defenses, Lorelai was right. Rory didn’t want to hear it, but this was also completely different from the situation with Jess. 

“I know…I’m so sorry I have no idea how that just happened,” Rory whimpered.

“Because you’ve been getting in the middle of that marriage for awhile now and I told you it was going to blow up in your face! Here’s the boom kid!”

“That’s not really my fault! Dean and I are friends, I knew him first!” Rory said defensively.

“Oh you don’t get to pull that card. You knew him first but you two broke up Rory. You were totally fine when you two broke up for the last time! You said that it was for the best and that you had been drifting apart for awhile. You don’t get to call dibs on him. Marriage trumps!”

Rory started to cry at this point, wiping furiously at the tears starting to come down her face. She didn’t want to admit how wrong she was, how foolish she had been acting for the past few months but her mother wouldn’t stop. 

Lorelai softened seeing her daughter’s tears. No matter how disappointed she was, she never could stand seeing Rory cry. It was like torturing Bambi.

“Look, I was coming to find you because I realized I forgot to get CDs for everyone who might want them later tonight. How about you go get them and take a break, think for a little bit.”

Rory nodded, appreciating the chance to get away from the craziness. She wasn’t sure how she was supposed to get excited and be supportive for her mother in light of what had just occurred in the past 10 minutes. It was probably a terrible idea for this to happen on the most important night of her mother’s professional career. 

“I’m really sorry mom. I really did not mean for this to happen right now. I’ll be back with the CDs,” she said as walked around her mother and hurried out of the inn. 

Rory almost ran from the diner all the way back to her house which was no small feat. When she entered the house she went to her room and laid down on her bed trying to catch her breath. She took her phone that had been on silent out of her pocket and discovered she had 1 missed call and a voicemail from Jess. She raised her eyebrows. She hadn’t heard from him in a couple days, both citing that they were incredibly busy. Jess was working against a deadline for the zine and of course helping her mom with the inn had Rory slammed. She didn’t expect to have time to talk to him again until at least tomorrow once people left but she welcomed the opportunity to hear his voice in this moment. 

“Hey, it’s me. Just wanted to see if you had a moment to talk or whatever. Thought I would try since I finished up a lot of stuff for the zine earlier than expected. Which is a miracle since Matt accidentally deleted like 3 articles and pissed off our comic illustrator who didn’t want to turn in his part. Anyway call me back when you can, wanted to tell you about the new author we’re publishing. I think you’ll like him.”

Rory listened to the voicemail twice before she began to cry again. The shame that washed over her was almost unbearable and she curled up in a ball on her bed. Maybe she and Jess weren’t a thing, but she certainly felt things for him. What was she doing juggling these two boys? If anything, her kiss with Dean earlier was confirmation that this was all a terrible idea. She should have known that before they kissed, but the physical part of their relationship was no longer going to be satisfying to her. After what she had with Jess, it was like another part of herself had opened up. She wasn’t sure that Dean could reach that in her.

It seemed naïve and ridiculous to even put Jess into consideration with this situation, but from the way the two communicated something was still brewing from what started on the lawn of the Independence Inn. As much as her mother wanted to simplify the whole thing into a one night stand, the entire encounter felt like an awakening for Rory. She couldn’t get it out of her head, she thought about the feelings he had evoked in her while she lay in bed at night trying to fall asleep. 

It was never something she’d done before, but the ache and feelings had been so much one night that she had to touch herself to reach a sense of relief. She’d mimicked the way Jess had touched her that night until she panted hard against her pillow, afraid of alerting her mother in the living room of what she was doing. 

These feelings coupled with the very real marriage that Dean was in even if he wasn’t happy were enough to cement the fact that Rory had to be completely done with Dean. No friendship. No talks in the hallway. No crying on his shoulder when she was having a breakdown about school. No calling him to come rescue her for any reason. It had to be all over. 

Rory laid in her bed for another hour or so before she was able to get up and begin to collect the CDs her mother needed. She had a slight headache from her crying but she would change into her dress, wash her face, and feel much better when she went back to the inn. She would put all her energy into making sure her mother’s night went exactly as she planned. 

She heard a knock on the backdoor when she was in the kitchen putting some more CDs on the table. She looked to see that the backdoor was open and yelled for the person to come in. She continued to arrange CDs into a tote bag as the door opened and looked up to see Dean nervously walk through the door. 

“Hey,” he greeted. 

“Hey,” she nodded.

“I saw that you weren’t around once I was done at the inn and I thought that this was a good place to look for you. Was your mom mad?”

Rory shook her head. “You have no idea.”

“I’m really sorry she saw us. But she’ll understand right? Since I’m leaving Lindsay? It’s not wrong.”

“Dean,” she pleaded. “You know it is. You’re married and you kissed me.”

“But-“

“I can’t do this,” Rory said definitively.

“What do you mean? The past couple months…I thought you felt it too?”

“I know you thought that. I thought I did too. But Dean when we broke up, we did that for a reason. At least I did. And maybe you feel like you made a mistake with Lindsay but whether or not you end it with her should be your decision and have nothing to do with me. I just don’t think I feel the same anymore.”

“But we can try?” he asked taking a step towards her. “It’s been over a year since we were together. We just need to try again!”

Rory stood her ground and shook her head. “No we can’t Dean. I don’t want to. I think you should go back to Lindsay. You either try again or you get a divorce but please don’t make this about us.”

Dean stared at her as if she was a stranger, and really she felt like it was becoming that way. She didn’t feel like the same person she was when she woke up this morning. She felt a little brand new because of her kiss with Dean, because even if it was a mistake it was a wake up call to the mess she was heading into. 

“Rory-“

“I think you should go Dean. I have to go back to the inn,” she told him softly. 

Dean continued to stare for a few moments and she could tell he wanted to say something else. Instead of continuing to look at him she went back to loading her CDs into the tote bag, signaling to Dean that their conversation was over. She heard him take footsteps towards the backdoor and the slam of the door made her sigh with relief. 

She washed up and put on her dress and went back to the inn with the CDs in tow.

***************

The next afternoon Rory watched as many of the townfolk exited the inn with smiles on their faces, gushing about how beautiful the whole experience was. She collected the feedback cards from Taylor with smile, even though he complained the whole time about how hard it was to get pencils the whole night. 

Lorelai had been busy enough that the two women didn’t have time to talk the whole night. Rory had waved the CDs to her mother when she reentered the inn the night before and then joined a table of friends for dinner. Her mother had been all around the whole night making sure that everyone had what they needed. She didn’t get up to their room until after Rory had fallen asleep. 

Rory was getting ready to go back to the house when her mother found her at the front desk. 

“Hey we’re supposed to have lunch with your grandmother.”

Rory’s eyebrows furrowed. “But she left?”

Lorelai shrugged in response. 

Rory sighed. “Fine, lead the way!”

The three women sat in silence at their table outside. It was a beautiful summer day and Rory sipped her iced tea as she watched the horses get groomed just outside of the stables. It was certainly a better view than her mother and grandmother in this moment. Both women were quieter than usual, stewing in their anger about who knows what. 

“So mom,” Lorelai finally relented. “When do you leave for your trip to Europe you were telling us about?”

“Oh I leave in 3 days actually. It’s going to be lovely. I haven’t traveled overseas without your father since I was in college. It’ll be very liberating!”

Rory smiled at her grandmother’s excitement. While she was worried about the state of her grandparents’ marriage, there was nothing wrong with Emily being excited about some independence.

Lorelai nodded. “It does sound good! Very exciting.”

“Yes yes. And Rory, the offer to escort you around Europe for the summer is still on the table. If you’d like to go it’ll be very easy to get you a plane ticket in the next couple days. Oh I’d just love to show you some of my favorite spots!”

Rory smiled. “Oh grandma that sounds great but-“

“I think it’s a great idea!” Lorelai interrupted. 

Emily and Rory looked towards Lorelai surprised. “What?”

“Yeah it’s not like you have anything going on this summer right?” Lorelai asked with an almost too bright smile on her face. Rory had been put into a trap and she knew it. She couldn’t exactly start a fight with her mom right in front of Emily. 

“No I don’t.”

“Then you should go!”

Rory looked at her mother with a look of disbelief on her face. Sure she messed up, but did that mean she needed to be sent away?

Rory looked towards her grandmother with a tight smile. “Can I think about it grandma? I will let you know tomorrow morning ok?”

Emily shrugged with an easy smile. “Of course dear! Take your time.”

Rory took another sip of her iced tea and got up from the table. “I need to go take a look at a couple things, decide if I’ll definitely go to Europe or not. Sorry to cut out on lunch grandma.”

“Oh nonsense. Go ahead and give me a call later.”

Rory nodded and waved at the elder Gilmore girls as she walked off shaking her head. She heard her mother excuse herself from the table in the distance and the hurried footsteps to catch up to her. 

“Hey kid wait up!” Lorelai said.

Rory stopped and waited for her mother to catch up before turning to her. 

“What are you trying to do mom?” Rory hissed.

Lorelai stumbled. “It’s a good idea for you to go away ok?”

“Oh what is this? You’re acting like I’m pregnant and you have to send me away to convent to ride it out quietly.”

“Hey that’s not what this is! I just think you need some time away from everything. Between the thing with Jess and now this whole thing with Dean I just think you’re not yourself.”

“I agree the Dean thing was a mistake mom. I talked to him yesterday and I made it clear that he and I were not going to happen again but you definitely need to let the Jess thing go. That wasn’t a mistake. And you can’t send me off to Europe and expect that my problems will go away.”

“This just isn’t you-“

“Of course it’s not! I don’t know I am!” Rory exploded. “I’m 19 mom. I’m not supposed to know who I am!”

Lorelai stood silently and said nothing. What else was there to say. 

“I’m not going with her mom,” Rory finished as she walked away.

***************

Rory spent the rest of the day in her room, staring at her surroundings. Lorelai obviously had a billion things to do at the inn so she didn’t expect to see her for the rest of the day and she was glad. She’d never been so disappointed in her mother, wanting to just send her away as if she was some problem that someone else needed to fix. Their relationship never worked like this, and the distress she felt in her heart was something she would usually go to Lorelai about. 

She couldn’t do this all summer. She couldn’t stay in this house, suffocating and tiptoeing around her mother and trying to avoid Dean. But she also didn’t want to traipse around Europe with her grandmother when it was something her mom wanted her to do so she could get away from problems that weren’t really problems. Where could she go?

At that moment her phone vibrated with a text message. She looked and saw it was from Jess, telling her about the comic their illustrator turned in late. He’d attached a picture of it for posterity. She looked and laughed, noting that it wasn’t at all funny and almost glad for Jess that it came in too late to go into the zine. 

She stared at her phone for a moment, her brain all of sudden waking up. She shot up from her bed and went into her closet digging out her small suitcase. She moved with purpose around her room collecting clothes, toiletries, and books she couldn’t live without. She took a couple CDs she would need for her car and loaded up her suitcase and backpack with all the items. She looked around the room again to see if she’d forgotten anything important before hurrying out of the house and to her car. 

Once she loaded everything in the trunk she got in the car and took a look at the house. She should probably leave a note for her mother but she didn’t exactly know how long she was going to be. She would either get a good reception and need to call her or it would be a bad one and a quick trip not worth mentioning. 

Rory started the car and took her GPS that her grandparents had bought along with the car and proceeded to put in the address for Truncheon books that she had seen when she researched it online weeks ago.


	6. Chapter 6

**Notes for the Chapter:**

> Surprised to be getting this to you so soon, but with New Years traveling and the end of my holiday coming up it seemed like the best option. I hope you enjoy it. Writing this story has been so fun so far and your feedback is always so great to read. A fun note: the title of this story is inspired by "Same Ol Mistakes" by Rihanna (originally by Tame Impala as "New Person, Same Old Mistakes"). There's something about this song that served as weird driving force for me to write this alternate universe along with a lot of the discussions I've had with fellow fans post revival. It's been great to listen to as I write this, hope you like the song as well :-)

Jess considered himself to be a realist. Most things in his life didn’t last forever and everything that occurred in his life taught him that. It was probably why it was hard for him to date long term. It wasn’t that there was anything specifically wrong with him since he was at the most stable place he’d ever been in his life. He had a job he really loved and was good at, he’d at least gotten his GED, he bartended at his neighborhood bar that felt like a weird but lovable community, and he had 2 people he actually considered best friends. So much of the strife he’d endured in his youth wasn’t a source of contention anymore, something about it had been resolved ever since he left New York. But that didn’t change that his mother was his biggest example of relationships and she wasn’t a very good one. It made it hard to know how to be with another person. 

So he dated, never for longer than a few months at a time. The girls were always cool, always the same type. Blonde, usually punk style, into the same music. He was able to deal if they weren’t big book readers, but they had to at least have some intelligence going for them to carry a conversation. The sex would always be good, he made sure that his partners were just as satisfied as he was. But after a few months he could never lay down an actual commitment. It would usually end once the girl started asking for labels, wanting to know if she could call him her boyfriend. He would consider it at first, just to be fair and see if this was the moment that he would break his patterns and cycles and see that the girl was worth doing that. He would take everything into account and usually his conclusion was that this wasn’t the moment to go off his usual course. 

Rory was off course though. It’d been a few weeks since he’d met her and he found himself thinking about her at odd times. Thinking about things he wanted to ask her, wondering if she would find something funny that he saw based on her humor he’d gotten to know in that short amount of time, and lying in bed at night wanting to kiss the indents of her collarbone. It was an odd feeling. 

He sat on his stool behind the bar at SPTR reading a book and coming up with excuses to go to Stars Hollow. He came up with none and it was actually disappointing. He had hoped that at some point he could convince her to make a visit to Philadelphia, especially because it was summer and the best time in the city to come visit, but he had doubts it would happen. He had many things pegged about her from his observations throughout the day he met her. 

Stars Hollow was a small town, the smallest of towns even. When he sat in the diner he could see that the cast of characters that inhabited it were incredibly tight knit, gossipy, and nutty but all in all they were a town with a lot of love. It was probably a great place to grow up with not a lot of room for rebellion. Rory was smart from what he could tell and getting into Yale was no small feat. She had to be the smartest in her class at Stars Hollow High. When she walked into the diner and around the town people looked at her with a soft look of admiration. She was the town princess, she was perfect. It put their time at the lake into perspective actually. Her mother probably never had the problems with her that his mother had with him growing up. Despite the conversation he overheard when he first met them, they seemed close and Rory also seemed to value her mother’s opinion a great deal. The way they bantered during the ceremony was an indication of a long built relationship between the two of them.

Her mother was not happy about what the two of them did and that is not a surprise. No mother would be happy about their kid going off and having sex with someone they just met so he really can’t blame her but it also means that there was room for Rory to have doubts about what happened. 

He hoped that she took his words to heart before he left. He hoped that his intuition and observations were right and that what they did was just as good for her as it was for him. And that that any doubts she may have wouldn’t stop her from making a visit so he could see if this was all a fluke.

******

By the time Rory parked her car along Locust Street where Truncheon was located it was close to 10pm. She hoped with all her heart that Jess was still there working late or that one of his coworkers who could direct her to where he might be was. It took a couple loops around the block to make sure she could find a parking spot, she got lucky when someone else was leaving so that she could take it.

Once she parked she left her big belongings in her trunk so that she wouldn’t have to lug it around the city. She walked the block she needed to in order to reach Truncheon, taking notice of the buildings along the street. It was a beautiful neighborhood, somewhat busy with young people obviously going out for the night and older couples walking their dogs. She reached the steps of her destination and was relieved to see that there was a light on in the front lobby. She tried to open the door and found it was locked. There was a note on the door with the store’s hours and it seemed they closed at 10pm. She was just in time.

She knocked and rang the doorbell a couple times and luckily only had to wait a minute before she saw a young light skinned black man coming towards the door. He had a confused look on his face but opened the door an inch just to poke his head out.

“We’re closed. Can you come back tomorrow?” he asked.

“I could but I’m not actually here to come to the store. Not that I don’t want to come eventually I just think I should find the person I’m looking for first before I even do that. Especially because I don’t have anywhere to stay tonight if for some reason I don’t find Jess or I’ve been an idiot this whole time and he thinks it’s crazy that I drove down here to visit him. I mean it’s crazy right? I don’t even know him and I guess he said I should come visit but I should tell him when I’m going to do that so he’s prepared in case-“

“You’re looking for Jess?” the man interrupts. 

“Yes,” she confirms.

“He’s not here,” he deadpans.

“Oh.”

“Yeah he’s at his other job. Bartender at South Philadelphia Taproom.” 

“Oh! Can you tell me where that is?”

“Sure…want me to write it down?”

“That would be so great!” she answers gratefully.

She waits a couple minutes while the man goes inside to write down the address for her and thinks about her options to get to her next destination. Hopefully this place is within walking distance and she can walk with her purse to get there. If not, she’ll have to drive but she definitely doesn’t want to do that since it took so much time and effort to get this parking spot. She can’t imagine she’ll have the same luck if she moves.

The man returns with the address. “I’m guessing you’re not from around here but this bar is in south Philadelphia. You’re in center city right now so it’s not exactly close. I’d say the best way to get there is to walk the few blocks to the broad street line and take it down to the Snyder stop. I wrote that down for you. Or you could drive.

Rory frowned at the paper with the address and vague directions written down. She considered her options for a moment before looking back up at her helper with a small smile. “Thanks for writing this down, I appreciate it. Sorry to bother you too. What your name?”

“Chris, I work with Jess here obviously. And you are?”

“I’m Rory.” She stuck her hand out for Chris to take hold of and shake.

“Well I hope you find Jess…and that you don’t get lost.”

Rory laughed nervously. “Yeah thanks I’ll try my best.”

Rory gave Chris a small wave as she went down the steps and looked around to figure out how to get to her destination.

“It’s to your left,” she heard Chris call out to her. She blushed and mumbled a thanks before heading in that direction. Chris laughed and shook his head, closing the door and getting back to his work.

******

Jess loved working at SPTR simply for the ebbs and flows that came with his nights at the bar. There were hours where it would become busy, but the patrons were never crazy college kids that wanted to party and get beer all over the place. He knew most of the people who came in here and it was usually for a good beer and some food either with a few friends or on a date. He was lucky that it was moderately busy and that he had Blake on hand with him in case more people came through.

He was pouring beers for a group of guys while Blake worked on some cocktails when he saw from the corner of his eye and new person walk into the bar. He couldn’t take too much notice of the person since he was in the middle of an order but he figured if they were alone they would come sit at the bar. He got the guys their beers and collected their cards, zipping through the computer system to open up a new tab. Once he was done he immediately looked around to make sure that people had everything they needed.

That’s when he saw her.

Rory sat herself in the middle seat of the bar, looking at him nervously and biting her lip. She looked the same as she did a few weeks ago, dressed in another simple dress to fight off the oncoming sweltering heat that comes with a Philadelphia summer. 

He walked slowly over to her, a smile creeping up on his face. He couldn’t believe she was here.

“Hey,” he greeted happily.

“Hey.”

“You’re here.”

“That I am. I’m pretty lucky I caught your friend Chris before he left and got the address here. And lucky that people in Philadelphia aren’t as harsh as they’re made out to be in the movies so when you ask how much money you need to get on the broad street line they actually tell you. And that I still have my fake ID that I got when I went down to Florida for spring break so it’s actually pretty good and I was able to get in here.”

“You’ve got a lot of luck going for you there. You look like you need a drink,” he notes amused.

“Do I? Do I look super stressed? Oh god,” she worries.

“No it’s not that…you look good. You just look like you need a drink to calm down.”

“Oh…I don’t really drink that much actually. Last time I did was spring break in Florida and it was weird and my friend Paris got the bright idea to kiss me to get attention and do spring break the right way. Maybe it’s not for me.”

Jess tilts his head and considers her for a moment. “You’re pretty nervous aren’t you?”

“How can you tell,” she responds sarcastically.

“Could be all the rambling you’re doing. Well let me just put one worry to rest-it’s good to see you.”

“Really?” she says hopefully. He nods in response.

“Oh good. Because I really made a last minute decision this afternoon to just come here. It seemed like a good time to do it since I don’t have anything to do this summer and my mom was hinting she wanted to ship me off to Europe with my grandmother because she thinks I’m making terrible decisions. I really need to stop rambling.”

Jess shrugs. “It’s cool. How about some water for now?”

“That would be a good start.”

Jess pours Rory a water and looks around at the bar to see how easily he can get away with a break to talk more with Rory. It’s just about 11 at this point and he has until 2:30 to be here. He hands Rory her water and goes over to Blake to see if he can handle the bar by himself for 15 minutes. Thankfully Blake is a cool guy and more experienced than he is.

“Hey,” he calls out to Rory, “let’s get you a table. You hungry?”

Rory scoffs. “I’m a Gilmore, I’m always hungry.”

“I don’t know what that means but I think I’m about to find out.”

Jess comes around from the bar and takes Rory’s hand so he can gently lead her off the bar stool. Instead of leading her to a table he pulls her into his arms a gives a firm kiss. Rory’s eyes widen in surprise, but they slowly close when it becomes clear that this isn’t a short kiss. Jess deepens the kiss, reaquianting himself with how good it feels to kiss Rory. He breaks the kiss with a smile.

“See? I am glad to see you,” he tells her before pulling her along to the table. 

The two sit down at a table in the corner and Rory sips her water now with a calmer look on her face, devoid of her previous nervousness. The two look at each other for a few minutes not knowing what to say now that they’re here with each other. 

“So you came to Truncheon first?” Jess starts. 

“Yeah I figured that was the best place to start. I parked my car over there with my stuff, I think it was pretty lucky that I even got a parking spot so I didn’t want to drive here.”

“Yeah I live a few blocks away from here and it’s hard to find a spot at this time. You can just get your stuff tomorrow I guess. When do you have to be back in Stars Hollow?”

Rory blushed at this question, because here came the point where everything became uncertain. “I don’t really have to be back…for awhile.”

“Awhile huh?”

“Yeah…like I said, no plans for this summer!”

“Ok…so how long did you want to visit?”

“I just figured I would stay until you got sick of me?”

Jess laughed. “You think pretty highly of yourself there.”

Rory shook her head. “Look I’m really sorry. I came here on a whim because it felt like I had to get out of Stars Hollow. It was either this or go to Europe with my grandmother and this honestly seemed like a better option.”

“I’m actually kind of flattered.”

“You should be. I mean I can go tomorrow if you want?”

Jess sighed and considered her for a moment. “We can figure it out tomorrow. It’s fine. I’m sure your mom wasn’t too happy with you coming to see me.”

“Well she doesn’t know,” Rory mumbled.

“What? Where does she think you are?”

“I didn’t tell her anything.”

“Oh you have to call her.”

“Why?”

“She probably thinks you’re dead in a ditch! Look you seem to be pretty close with your mom and I’m not trying to get in the way of that so leaving the house and going to another state without telling her is not something I’m going to tell you to cool to do. You should at least call her and let her know you’re alive.”

Rory looks away from him embarrassed. The fact that she is a few years younger than him comes back to Jess in this moment. This want to stray away from the nest, to be independent without consequences…this is what she’s dealing with now. It’s normal but it’s far off from where he is in his life.

“You’re right,” she confirms.

Jess looks at his watch and then looks around at the bar. It hasn’t gotten busier, but he should get back to work before the manager in the back notices he’s slacking off. 

“Look I have to go back to the bar so you have a couple options: you can stay here until I can get away probably around 1 and we can go back to my apartment or I can give you the keys now and you can go ahead. Order whatever food you want too, it’s on me.”

“Oh…I mean I can stay until you’re done. I don’t want to take you away from work. I have a book here I can read and I think as long as I have some fries I’ll be good.”

“Cool. I’ll put in the order for those fries. Just come to the bar if you need something.”

She nods and gives him a small smile as he gets up and hurries back in time to take the orders of a new couple that came through the door to the main bar. Rory watches as listens with a smirk at the story the couple tells him. He seems to know them and talks with them for a few minutes as he makes them some cocktails. She pulls out her book, Anna Karenina for tonight and sips her water. The candlelight is really her only source of light and she revels in it, loving how cozy this bar is.

****

Jess checks on Rory throughout the next couple hours but there comes a time around 1am where he loses track due to all the people starting to clear out. He’s closing tabs, exchanging jokes with some regulars and by the time he looks back at Rory around 1:30 he finds that she is asleep with a serene smile on her face. Her book is open in one hand, her thumb slipped in between the pages, her other arm curled under her head to make a pillow for herself. The candlelight creates a glow on her face and Jess can’t decide if he likes it better than the glow the moonlight shines on her face. 

He looks to Blake and asks if he minds him cutting out early so he can get Rory to his apartment. Thankfully Blake is the best person ever and tells him not to worry about it. Jess collects his tips and thanks Blake again as he hurries over to Rory to wake her up. He bends down next to her seat and gently shakes her shoulder, whispering her name. Her eyes open slowly and she looks to Jess blearily. “Home?” she asks.

“Yeah,” he says with a small smile.

She gets up with him and puts her book in her purse. He can see she can barely keep her eyes open and slips his arm around her waist to guide her out of the bar. Thankfully he’s only 2 blocks away and the walk should wake her up enough to make it over there.

They walk slowly but silently back to his apartment, Rory slowly becoming more awake after at least a block. She finds this neighborhood is different than where Truncheon is, primarily made up of old rowhomes. The neighborhood was quiet, but she could hear how lively it was as they passed some bars that were close to last call. They reached an apartment building after another block and Jess quickly let them inside. Rory was glad to see that he lived on the first floor and they didn’t have to climb any stairs. 

Jess’s apartment was simple with a table and chairs, couch, a small tv, and many bookshelves full of books. She would make sure to examine his collection tomorrow when she wasn’t so tired. At the sight of his bed once they entered his room she felt the exhaustion come over her again, eager to burrow under the covers and fall asleep. Jess let go of her waist at this point, going to his dresser and producing a tshirt for her to wear. 

“Here, you can wear this. If you want pants I can find some boxers for you but it gets pretty hot in here even with my window unit on.”

She blushed, almost shy of wearing just a tshirt and laying in bed with this man, but considering that she’d already had sex with him she had to take a deep breath and consider this wasn’t a big deal in the grand scheme of things. She took the shirt and went to what looked like his bathroom to change and wash up.

When she came out she found that Jess was already in bed, looking through his phone with furrowed eyebrows and dressed only in some boxers. She put her folded up dress and bra on top of his dresser and shyly got in his bed with him, placing herself right at the edge so that she didn’t crowd his space. Jess looked over at her intrusion and raised his eyebrow at her distance. 

“You can come closer you know?” he told her jokingly.

“I didn’t know if you liked to cuddle,” she told him as if it was obvious.

He scoffed and pulled her so that she was against him, reaching over her waist until her head was resting on his arm. She looked up at him and he kissed her cheek. 

“I am glad you’re here Rory. We’ll get you that cheesesteak tomorrow.”

Rory laughed. “I’m going to hold you to that. Goodnight Jess,” she said closing her eyes.

Jess murmured a goodnight but did not close his eyes. It took him another hour to fall asleep, thinking about what this girl was doing in his bed, in his city even though it’s what he’d been silently hoping for the past few weeks. But now that it was here he was incredibly confused as to why it was happening. He hoped she had better clearer answers in the morning.


	7. Chapter 7

**Notes for the Chapter:**

> Happy New Year! It’s funny how with fics you don’t know where you’re going with it until all of a sudden you do. That’s where I’m at with this. I’m also excited because I live in Philly and this is my favorite place in the world so it’s kind of a weird love letter to my city. Thanks for reading!

Rory eyes popped open at the continuous sound of her ringing cell phone in the distance. Jess’s room had a blue glow as it was not quite sunrise but not night anymore. She glanced over at the clock and saw it was 4:15am. She unwrapped herself from Jess’s arms and tip toed over to his dresser where her phone continued to ring and vibrate annoyingly. She sighed when she saw her mother’s name on the screen knowing she was about to hear an earful. She never did get around to calling her last night. She really intended to, but then she fell asleep at the bar and couldn’t wait to get in a warm bed after she and Jess walked home.

Rory continued to tip toe out of the bedroom into the small living room and answered the phone. 

“Hey mom,” she whispered.

“Hey mom?” Lorelai said incredulously. “You’ve been gone for almost 24 hours with no word and haven’t answered your phone and all you can say is Hey mom? I called Lane and Paris, which was completely torturous by the way and she is probably leading a SWAT team to make sure you’re ok. I almost called my parents to make sure you didn’t disappear over there, I’ve walked all over the stupid town twice with Luke and finally you answer the phone and all you have to say is Hey mom? Where are you?”

“I’m…I’m in Philadelphia.”

“You’re in Philadelphia?” Lorelai cries. “What the hell are you doing in Philadelphia? What could you possibly have to do there?”

“I just needed to go ok? I needed to get away. I should have told you but it came to me after you left.”

“You were going away, you were going to Europe with your grandmother!”

“Which is what you wanted! It’s not what I wanted!”

“So you decided to run away without telling me?”

“So you could judge me all summer? Or send me off to have guided fancy tours of Europe with grandma? I wanted to do something so I did it. I’m really sorry I didn’t tell you but I thought it would be a good idea for me to just go.”

Lorelai was silent for almost a minute, and even though Rory couldn’t see her mother she could imagine the angry pout that had overtaken her face. She loved her, but at times like these she would revert to an angry teenager. 

“When are you coming back?” Lorelai finally asked.

“I don’t know,” Rory answered quietly.

“You don’t know?”

“I just need some time away!”

“No you don’t Rory. You were getting time away from everything before-“

“But it was totally controlled by you! You were sending me away like you were Emily or something so yes I ran away. I ran away from you!” Rory hissed.

Lorelai’s gasp and silence was palpable, the immediate hurt came through like waves. Rory almost didn’t believe herself, her eyes widened and hands shook. 

“Mom,” Rory whispered shakily.

“No I hear you. Are you safe out there?”

“I…I am. I’m staying with Jess.”

“Oh.”

“Mom, please.”

“Make sure you stay safe. I guess I’ll see you when you decide you’d like to see me huh?”

Rory thought for a moment as her next words would very much determine how close she and her mother remained for the time being. Despite how hurt they both were, Rory longed for the fun moments between the two of them where they could laugh and talk about anything. But maybe this was a lesson that everything didn’t include some things.

“I love you mom. I’ll call you soon,” she conceded.

“Bye Rory,” Lorelai finished shortly before hanging up the phone.

Rory closed her phone and took a deep breath. She asked for this by running away, she couldn’t be surprised by her mother’s anger. 

After sitting awhile to calm down, Rory walked back into the bedroom and saw the sun was just beginning to rise. An almost pink glow was coming from Jess’s window and she smiled at how the light created a halo around him in his bed. He was incredibly peaceful and vulnerable when he was like this. He had a pensive look on his face as he slept and she wondered what was on his mind. Was it the next great novel he was about to write? How to weave a new plot that was just as much the right amount of cynicism and optimism that The Subsect was? She wondered how his life informed his writing, if it had hardened him enough that the pain that came through in his work was easy to write down at this point. She wanted to wake him up and make him tell her everything.

She slipped back in the bed quietly so not to wake him, facing him this time instead of sleeping away from him. She was afraid last night, never sleeping a full night with a boy before. But facing him now when he was asleep created safety so that she could fully examine this man that she’d decided to run to. She didn’t know if she was going home today, tomorrow or next week but he had said multiple times that he was glad to see her, and she had no choice but to believe him.

She watched him, until her eyes grew heavy and again and she went to sleep.

***  
Jess woke up next a couple hours later disoriented and confused to see Rory sleeping next to him. She faced him, arms curled under her head in a fetal position, her eyebrows furrowed and lips pursed. The little breaths that came in and out of her mouth felt like wisps on his nose. He remembered the previous night and smiled, glad that it wasn’t a weird and very realistic dream. He reached out and wrapped his arm around her waist to bring her closer to him. He leaned down to kiss her cheek lightly, remembering how her skin felt like porcelain when he was with her a few weeks ago. He trailed a series of soft kisses from her cheek down to her neck, sucking on her pulse point until he felt her wake up and giggle hoarsely. 

“That tickles,” she said, her voice still full of sleep. Her voice was deeper when she woke up, sexier and he liked it. He groaned feeling her body become pliant against his, wrapping her arm around his neck so that their bodies were in sync with each other. 

“How’d you sleep?” he asked sleepily against her neck.

“Ok…until I woke up to my phone ringing.”

“I guess that’s what I kept hearing all night. Good thing it didn’t keep me up.”

“Oh God I’m sorry!” Rory cried. “It was my mom. I totally forgot to call her last night since I fell asleep at the bar so she definitely was calling me all night.”

“And I bet she was pissed when you finally answered the phone,” Jess predicted. He felt Rory nod against him. 

“Yeah. It was probably the worst fight we’ve ever had,” she noted sadly. “She and I don’t fight. And when we do we make up so quickly, I think the longest has been a day and it usually just takes one of us getting tired of the silent treatment and we fix it with a movie night. That’s not going to happen this time.”

“She can’t be that pissed about you and I. It’s really not a big deal.”

“It’s not just you and I. She was able to ignore that after some snide jokes and us yelling at each other. It’s something else.” Rory didn’t want to tell Jess about Dean but it almost seemed right to do so. She wasn’t obligated towards Jess, they weren’t in a relationship, but it had seemed kind of wrong to have a one-night stand with one guy and then go and make out with your married ex-boyfriend. 

“Oh?”

“Yeah.”

Jess let the silence hang in the air for a moment. “Do you want to talk about it?”

Rory thought to herself for a minute. Jess was incredibly helpful and non-judgmental the last time she opened up to him even a little bit. He also seemed very observant. The worst that would happen is that he’d think she was a horrible person and kick her out of his apartment and she’d have to go back to Stars Hollow with her tail between her legs. Maybe she would visit Christopher and Sherry in Boston, get to know Gigi a little better. The thought made her shudder though. Lorelai would flip if she figured out that she ran to her almost stepmom.

“I guess I could?”

“Are you answering a question with a question?”

“Maybe? I just don’t want you to get a bad impression of me.”

“I’m not really in a position to judge, I learned that a long time ago,” Jess reassured her.

Rory looked up in interest. “What’s that supposed to mean?”

“Oh that’s a story for another day, but no deflecting. Talk.”

Rory adjusted herself against Jess so that they were still wrapped around each other but her head was able to lay on the pillow and look at his face.

“I have this ex-boyfriend…his name is Dean.”

“Mmm the boyfriend.”

“We dated through most of high school. He was a good boyfriend, nothing wrong with him but we broke up senior year because he thought I would forget about him with college and everything. I got over it, he moved on and married this girl in September.”

“What a way to move on.”

“It was. And I felt strange at first but I was so busy with Yale that I didn’t have time to think about it. Until things at Yale weren’t what I expected and I started coming home more often. And he was always around, working at the market and helping with construction at my mom’s inn. This one time I had a breakdown because I was told I had to drop a class and I couldn’t find my mom and he was there. He comforted me a lot, he was always good at that. That was probably my first mistake, letting him do that for me. Because then we started talking more often and he would tell me things about his marriage. Like how he wasn’t going to school so he could work more and make money for he and Lindsay. She wanted a townhouse and he had to make sure she got it.”

“Sounds a little whipped if you ask me,” Jess scoffed.

“Maybe. I even talked about how selfish she was in the middle of the market to my best friend Lane and she overheard me. It was so embarrassing.”

“Who knew you’d be such a shark with that sweet face?”

“Shut up!” she laughed. “She didn’t want him to talk to me anymore and we ran into each other at the inn. He told me it wasn’t working with Lindsay and that he still loved me. And then we kissed in the hallway until my mom caught us. So here we are.”

Jess raised his eyebrow. “So you made out with your married ex-boyfriend.”

“Yup”

“You sure know how to step in it,” Jess noted. “I’m actually not surprised your mom was pissed.”

“It gave her license to bring you back up again,” Rory huffed. “We had lunch with my grandmother the next day and she’s going to Europe and my mom offered for me to go along with her. As if she’s sending me away like it’s all a shameful scandal.”

“So you came here,” Jess realized. 

“It seemed like a good idea at the time yesterday,” Rory said sheepishly.

Jess sighed, realizing he was now in the middle of a big family conflict, which wasn’t his idea of a good time at all. 

“Does it still seem like a good idea?” he asks.

“It does. As long as you don’t think I’m some freak or anything. I mean kissing Dean made me realize that I don’t even feel that way about him anymore. And I told him so. I told him to go back to his wife or divorce her but it had to be about him and not about me. I wasn’t going to be waiting for him.”

Jess looked at Rory with a thoughtful expression. “What was wrong with the kiss?”

“What?”

“Seems like you and this guy meant a lot to each other so what was wrong with the kiss?”

“It just,” she starts, “it lacked…something. When I was with you a few weeks ago I never felt-“ she stopped realizing where the discussion was going and blushed. Jess smirked and Rory wanted to smack it off him. She walked right into that. 

“So that was a good night for you?”

:”I thought we established that you didn’t need me to tell you that!”

“Oh but I do, because knowing without a doubt that I made you feel that good brings me just as much satisfaction.”

“You’re sick,” she laughs. “I don’t know why I’m staying here, you’re crazy.”

Jess laughs along with her, leaning over to give her a long kiss that quickly heats up. He rolls himself on top of her and grinds himself against her, bringing a drawn out moan from both their mouths. He reluctantly breaks the kiss to lean his forehead against hers. 

“Thanks for telling me all that. I’m sure that was hard,” he told her sincerely looking her in the eye. 

“You’re not mad?” Rory asked surprised.

“Let me put it this way without sounding crude: I could be mad but considering that a. We’re not monogamous, b. You didn’t sleep with the guy, and c. You’re here in my bed I think that draws a clear picture that there’s nothing to really be mad at.”

“How mature of you,” she responds sarcastically.

“All that experience of mine I guess,” he boasts. “Look you can stay here as long as you want. It’s not an issue with me.”

Rory’s face brightens. “Really? Are you sure? Because I don’t want to get in your way and make you feel like you have to entertain me all the time. You seem to have a couple jobs that keep you busy; you didn’t mention that you were a bartender before. And you’re probably busy writing a new book and here I am messing up your muse and distracting you.”

“You’re not distracting me. Plus I don’t have two jobs, Truncheon is my main income but I do a couple shifts at SPTR every now and then because I like the place so damn much. They also had someone call out sick last minute. I’m their fall guy.”

“That’s very dependable of you,” Rory teases.

“That’s me, dependable Jess Mariano.”

Rory giggled and raised her hand to trace the outside of Jess’s lips, focusing her fingers on the part of his smile that goes crooked, curious about what causes it. This was a good guy she realized. Most people, including herself, wouldn’t have listened to her story without a lot of judgment and that much patience. Except Lane. He reminded her a lot of Lane actually. 

He playfully opened his mouth and took her thumb in his mouth, biting it lightly. She yelped in surprise. 

“Are we done talking now?” he asks.

“Why do you have some grand plan for today?”

Jess traced his hands up Rory’s leg until he reached her panties and played with the hem. Rory blushed remembering that she came to bed only in an oversized tshirt the night before. She of course was not yet used to being so exposed in front of another man before. Jess took notice and kissed her cheek in reassurance.

“I realized I didn’t give you a proper welcome to Philadelphia. You were pretty tired earlier,” he told her coyly. 

“A proper welcome?”

“That’s right,” he eased one side of her panties down. “The Philadelphia special we’ll call it. And after that I unfortunately have to go to Truncheon for a few things but you can come with, get your car, and we can get you a cheesesteak for lunch?”

Rory’s expression came alive at the mention of food. “A cheesesteak!? Are we comparing Pats and Genos? I’ve read all about that. I have a lot of thoughts.”

Jess grimaced. “Oh we are not going there, if you make me go there you’re not getting the Philadelphia special.” He had taken his hand off her panties with a raised eyebrow.

Rory pouted. “This doesn’t feel like a warm welcome anymore. Fine I’ll trust your judgment.”

“Good, because I sure don’t want to be a bad host,” he said before taking her lips in a hard kiss and reaching to fully take her panties off. Rory moaned and her mind went blank, giving into the complete bliss and distraction that Jess was offering. Her mom was incredibly angry with her and she was in a completely new city but this man and his hands pulling at all these special places in her body put her troubles at ease. She wasn’t sure what would happen for today but for now she would give in to her natural senses. 

All that could be heard through the room for the next hour was the rustling of sheets grasped by hands and Rory and Jess panting, trying hard to hold back and not lose control despite the frantic way their bodies came together.


	8. Chapter 8

Rory didn’t quite know how she felt about Philadelphia yet. 

It wasn’t really that clean. When she and Jess walked along Broad Street she was surprised by how much people littered. She was also confused as to why people were allowed to park their cars along the median of the road. 

“Aren’t those cars going to get towed?” she asked Jess curiously.

Jess smiled at her wonderment. “No. The PPA, the parking authority, definitely rules different parts of this city but this isn’t one of them. People do what they want down here in South Philly.”

The architecture was grand in some places. As they got closer to city hall she stopped to smile at the pretty picture it made. There was trash everywhere and she’d run into more homeless people than she’d ever seen in her life but seeing the tunnel vision that historic building created on this main, busy street brought some clarity to the city’s charm.

“I hope you don’t want to go to city hall,” Jess groaned. “Are you one of those super touristy people?”

“Well no. I’ve been to New York a few times. We always try to make it to Times Square, it’s first on the itinerary.”

“Oh geeze.”

“I’m kidding! I’ve only been once. It was only worth it for the Tower Records and M&M store. But I’m sure you could find better record stores in smaller neighborhoods.”

“Oh for sure. There’s this one store I used to go to all the time, very off the beaten path. The guy who owns it was a genius, could point out any record by memory if you just gave him the artist and title.”

“My friend Lane would die there I’m sure. Did you live in New York for awhile?” she asked looking up at him as they walked.

He nodded. “Born and raised. I left when I was 18 though, did some traveling, and ended up here.”

“So how does Philadelphia compare? People always try to compare the two.”

He smirked. “They do. And it’s an unfair assessment for a few reasons. I’ll let you be the judge of how they compare though. I don’t want to bias you.”

“You could be giving me a hint,” she countered.

“No you’ll figure it out the more time you spend here,” he winked.

She shook her head in amusement and they walked silently on their path. She let Jess lead the way after another 15 minutes they encountered a busy, lively street. There were small shops everywhere with vibrant clothes, hats and accessories. She saw kids and teenagers weaving in between the crowds laughing and chasing each other. Some places were playing music that boosted fun punk sounds she recognized to booming rap music. The craziness of the street caused Jess to take her hand so that they wouldn’t lose each other and she took that as reassurance that she could continue to observe while he led the way. At one point they passed a huge window display full of condoms and…dildos?

Jess looked back and slowed down when he saw her disgusted face and chuckled. “That would be Condom Kingdom. You wanna go in?”

She shook her head vigorously. “No thank you. That’s definitely not for me.”

Jess continued to laugh and kept going, not wanting to embarrass Rory any further. He’d figured out after a couple sexual escapades with her that her inexperience didn’t mean she wasn’t open to sex, it just meant she needed someone to push her a little further. He was determined to get her to really voice what she wanted out of him. While he loved taking that control with a woman, there was something about Rory that made him want her to take some control, be forceful. It seemed completely against her nature, but so did her reactions when they had sex. 

Earlier in the morning he’d managed to get her to sit on his face, mostly because he loved the reactions he got out of her the first time he ate her out. Her face was beet red and she’d sputtered out many reasons why they shouldn’t do that, but all he had to do was give her a sweet smile and tell her to trust him. And once he’d gotten a few licks in and clenched her ass, because she seemed to really like that last time they were together, her body took over. She held onto his headboard, undulated her hips, and tried so hard not to scream out when she came. He liked her like that, struggling so hard not to go out of control. He focused on pleasuring her the whole morning, relieving himself in the shower while she’d taken a nap out of exhaustion. He would have had sex with her, but he was out of condoms. It’s not like he was expecting anyone.

Jess led them along the street until they reached their destination, a small restaurant stand called Ishkabibbles that boasted expert Philly cheesesteaks and a recommendation from Matt who seemed to love it. The sign had bright colors, hot pink and orange and that along with the name made him think the quirkiness of the establishment would be to Rory’s liking. She looked up and laughed at the name and he knew he’d done a good job.

“So here’s the thing, we’re very straightforward in Philadelphia so you have to know what you’re gonna get,” he explained. “You can get American, Provolone, or Cheese whiz-“

“Cheese whiz!” she exclaimed. “Oh god I love this place already.”

“I bet. You can get onion and hot peppers on it too but don’t go crazy or I’m sure they’ll kick you out. Just say you want one with whiz and then onions and peppers if you want it.”

“One wit wiz, got it,” she repeated. “This seems very complicated. What will they do if I do it wrong?”

“I told you, they’ll kick you out,” he deadpanned.

Her eyes widened. “I thought you were joking, you do it for me!”

“Oh no, you wanted a cheesesteak so now you have to work for it.”

She sighed and resigned herself. “Ok let’s go. But cover for me if I freak out, this is a lot of pressure.”

The two walked up to the window hand in hand, Rory bracing herself with a brave look on her face. Jess smirked…it really wasn’t THAT big of a deal after all. 

****  
Jess and Rory walked into Truncheon a hour or so later laughing and happy, full from their cheesesteaks. 

“Ok so I’m going to have to go there again before I leave for sure. It’s a perfect food delivery system-bread, meat, processed cheese and the occasional vegetable,” Rory marveled. 

“I see you’re glad you came all the way down here for that. It’s not the only good cheesesteak place around here though.”

“It’s not?”

“Nope.”

“Oh you shouldn’t have told me that. This is about to be The Great Philadelphia Cheesesteak Tour.”

“I’d really like to see you try,” he challenges her. Rory scoffs.

“I totally forget you don’t know me very well. You’ll regret that challenge.”

He shakes his head in amusement and looks around his workplace to see Chris and Matt heading towards them with curious eyes. He groans inwardly, mostly because the two of them bust his balls incessantly about women. Anytime a girl shows moderate interest in him it becomes a celebration and the Spanish inquisition. They’re determined to get him off his pattern of serial dating and every girl he meets seems to be the perfect way to break that pattern to them. He gives Rory an apologetic look before pointing out his two friends.

“Rory, this is Chris and Matt. They own this place and they’re the ones who brow beated me at the bar until I would come work for them. I guess you can call them my friends.”

“Oh it’s like that now huh?” Chris responds with his hand over his heart. “You’re gonna just deny me?”

Matt shakes his head. “He’s been waiting for the perfect moment to just abandon us you know.”

“He only wanted us for the endless supply of books Matt, we knew this. We knew he’d break our hearts!”

Rory giggled behind Jess while he rolled his eyes. Ever the jokesters his two friends.

Matt and Chris looked over to Rory at the sound of her light giggles and smiled genuinely. Chris reached his hand out to Rory first.

“Nice to see you again Rory. And to see that you made it over to South Philly ok. I was thinking that you would run into the 89 cent guy and it would scare you away.”

Rory frowned in confusion while Chris and Jess laughed loudly. “Who is the 89 cent guy?”

Matt cut in, “He’s this guy that wanders around the city and begs for money but he specifically asks for 89 cents. It’s totally confusing! We’re not exactly sure if he’s homeless but we’ve seen him anywhere and it’s just so weird.”

“That such an arbitrary number!” Rory exclaimed.

“Exactly!” all three boys laughed. 

“Ask me for 25 cents and I’m your girl.”

“He’d definitely make more money if he just did that,” Matt countered. 

The foursome walked further into the bookstore after that and Rory took a moment to look around the store. It was bookshelves on bookshelves but she loved the little nooks of spaces where you could obviously sit in a fun comfy chair and read. There were fun benches against some of the exposed brick walls gave everything a funky vibe. Jess led her towards the back that seemed to serve as an office with 3 desks with computers, scattered lamps and lots and lots of paper. She saw a huge old printer in the back and inhaled the smell of fresh paper and ink with a smile. This was heaven.

“So Rory,” Matt interrupted. “How do you know our fair Jess?”

“Oh, well I met him when he came up to my hometown for his mom’s wedding. His uncle has been giving me coffee since before I should have been able to drink it.”

“You met him at Liz’s wedding? That’s why you had a stupid secret smile on your face when we asked you how that was,” Matt teased. 

Both Jess and Rory blushed at this comment, Rory sneaking a glance towards Jess to see how he reacted. She felt like they were in elementary school, too scared to really let on that they liked each other. She was also relieved to see that he wasn’t one of those guys that went around bragging about his sexual conquests to his friends. That would have been embarrassing.

“Alright boys that’s enough,” Jess waved off. “I have to call that potential author in New York and Rory came here to get her stuff from the car. She kept demanding to see the place so we stopped in. But let me get her out of here before you embarrass me even more.”

The boys scoffed and shouted out unintelligible protests that Jess rolled his eyes at and Rory grinned. He took her hand again and hurriedly led her through the shop back to the warm sunny day. They ran out laughing and smiling just as much as they did when they first came in and Rory led them this time, immediately remembering where she parked her car a couple blocks down. They walked in silence, Jess swinging their arms a bit and holding her close. 

The whole morning and afternoon had felt like a dream to Rory. Here was this man, incredibly hot, intelligent and well read who wanted to listen to her problems and pleasure her endlessly. She’d been reluctant to get on top of him that way this morning but once he’d convinced her, the only thing she could think about was how good it felt. Sex had never been that good or adventurous for her with Dean, but all Jess had to do was touch and kiss her and she felt on fire. They didn’t even have sex this morning but it was still scandalous and irresistible to her as she thought about it now. She had a feeling Jess would keep pushing her limits if they kept on like this and she wasn’t entirely sure how to handle it. It wasn’t a bad thing…but she was certainly afraid she wouldn’t live up to the other partners she knew he’d had before.

She found her car and immediately went to the trunk to make sure no one had broken in during the night and stolen her things. She was relieved to see that everything was still in its place. She closed the trunk and opened the driver’s door, feeling Jess’s eyes on her. 

“Here are some spare keys to the apartment so you can get back in. I’ll probably be back in the next few hours or so once I can get away, I don’t have too much to do today. Plus it’s Friday, early day. You have a fake ID right? That’s how you were able to get into the bar last night?”

“Yeah, my roommate Paris made me get one before we went to Florida for spring break. Made sure we could get the most realistic IDs money could buy and then ranted so much about them that we got them for $10,” Rory answered proudly. 

Jess smirked. “Sounds like a good friend to have honestly. The guys wanted to go to this bar The Dolphin tonight. It’s a good walk from the apartment but it’s a cool scene. They’ve got a DJ doing an 80’s punk thing tonight. Cheap drinks, big light up disco wall. I like it enough.”

Rory nodded in agreement. “Sounds good to me I guess. As long as I can get in?”

“Oh we’ll sneak you in if not. Matt and Chris are good at distraction.”

“I look forward to seeing that,” she grinned.

Jess looked at her for a moment with a smile before coming back to himself. “I’ll let you go. Let me know if you have an issue getting into the apartment, help yourself to the sparse amount of food in my fridge. I’ll be back soon.”

He reached out to pull her to him for a long kiss, taking control and softly prying her mouth open to explore with his tongue. She whimpered, wrapping arms around his waist and falling against her car. His arms went to her face, holding her cheeks gently in contrast to the frantic style of his kiss. As the minutes went by it became slower, Jess sipping from her lips unwilling to let go. Rory pulled back so she could breath, panting against Jess’s lips. “I can’t catch my breath.”

Jess moaned against her lips and gave her another quick kiss. “You’re not supposed to. God I just wanna go back home with you right now, pick up from this morning.”

Rory slipped her hands under Jess’s shirt, squeezing his waist. “I think you had enough this morning sir.”

“But I want more, I want it all,” Jess whispered against her lips. He brushed his thumbs against the apple of his cheeks and inhaled hard. He wasn’t sure what this girl was doing to him but all he wanted to get in her car with her, drive back to his apartment and spend the rest of the day and night in bed with her, responsibilities be damned. “Can’t get enough of you Rory.”

Rory faltered, not knowing how to respond, especially to someone who seemed to want her so much. She’d never been face to face with this much desire. She took her hands from under his shirt and pushed him away with a hesitant smile. 

“You need to go back to work, I’ll see you tonight though.”

Jess sighed and conceded, letting go of her face and placing one last sweet kiss on her cheek. 

“You’ve got me a little addicted Rory Gilmore, I’m going to admit,” he told her honestly. He stepped away and gave her a wink and a smile before hurrying back to Truncheon. He left Rory with a bewildered expression that left her thinking for a few minutes before she got in the car.

This was intense.

****  
Jess’s apartment was almost as much of a literary haven as his bookstore. Rory had no idea how she was going to leave.

She spent the afternoon intermittently sleeping making notes of Jess’s books. She was pleasantly surprised by some of the books he already had and took notes on what was missing and completely necessary for his collection. She’d gotten hungry at one point as the day came to a close and sun started to set. She thought Jess would have been back by then but unfortunately he wasn’t. She was able to find some peanut butter that didn’t look deadly and took spoonfuls of it to pass the time. 

It wasn’t until almost 7 when Jess came through the door nonchalantly. Rory had finally finished all of the British classics Jess still needed for his home collection when he did so and had eaten half the jar of peanut butter. He saw the picture she made in his simple and meager apartment and his stomach clenched. He didn’t like how much he liked this. It could really only be temporary in the end. 

“Looks like you made yourself at home,” he observed.

“You have no food!” she argued.

“You’re right. Could have ordered some pizza though.”

“I didn’t know what was around! I can’t just order any pizza. It has to have the right price, crust softness, pizza to cheese ratio, delivery guy cuteness. There’s a system to this!”

Jess shook his head. “I know a place. You down for some square pizza?”

Rory hesitated. “That sounds weird.”

“Trust me,” he implored. 

She raised her hands up in consent and allowed him to pick up his phone and order a pizza for them. They spent the next few hours laughing about Jess’s day and arguing about the books Rory argued that he needed as part of his collection. He grimaced at some of her choices, but let her state her case and watched her with amusement as she passionately argued for why certain authors he’d never had the urge to read were necessary for his literary growth. He liked the fire he saw in her when she caught onto a topic she was passionate about, seeing her intelligence shine through. They were qualities that lit up everything about her that was already alluring. 

When their pizzas came, Jess took a couple of yuenglings out of his fridge and handed one to Rory. “It’s a Philadelphia institution, just as important as the Philadelphia special,” he winked. 

Rory took the beer and took a small sip of it. She didn’t like beer all that much when she went down to spring break but she was willing to give it another try. It wasn’t bad, but it was still a foreign taste to her. She took another sip and set it down as she ate her pizza, but found that the two actually paired quite well together. Jess took a look at her thoughtful face as she ate and drank.

“You don’t need to drink it if you don’t like it,” he assured her.

She shrugged. “It’s not bad.”

He smirked as he continued to eat and watched her eat almost half the pizza and easily finish her beer. She was full of surprises and he was starting to really like pulling them out of her.

***  
Rory had never been to a club before in all her 19 years and was sincerely surprised that she was even able to get into this one.

She didn’t know whether to call it a club or a bar though. She and the boys had set up shop at the bar so far all night. She shyly cheered on as the boys took shots and Jess scouted slyly scouted girls for Matt and Chris to talk to. When faced with the prospect, Chris seemed much more shy than she expected him to be and needed subtle encouragement and a pat on the back from even her. It wasn’t until a song by The Misfits came on that he felt empowered enough to drag Matt along with him to talk to the two fun girls dancing by the wall. Rory and Jess laughed together as Chris stumbled in nervousness and Matt gave them a scared look.

Jess looked over to Rory who had been slowly sipping a couple Yuenglings all night. This was clearly not her element, but the music and the alcohol had helped to loosen her up. She seemed to get along great with the guys, but she had such a calm spirit about her that he wasn’t surprised that they also took to her. 

She bopped along playfully to the music while she sipped her beer, glancing around at the crowded bar. He saw her gaze kept going towards the big disco light up wall that was the star feature of this bar. He heard the sounds of his favorite song, Guns of Brixton, slowly creep in throughout the bar. He gave a woop with the rest of the crowd to let the DJ know he was doing a good job and was surprised to see Rory was joining right along with him.

“This is my favorite song!” she bounced up and down in excitement.

He couldn’t help the affection he felt in that moment, knowing in that moment that this could go along with all the other things the two of them had in common. She jumped and swayed along happily, letting the alcohol take over her body and guide her movements. He bobbed along with her and took her hand, leading her over to the dance floor and closer to the disco wall she was so entranced by. 

He was able to get them to the wall and the bright lights shined on her face. She gazed into the light in wonderment, momentarily distracted from dancing. He took that opportunity to draw her into his arms and sway slowly to the music. She melted into his arms and wrapped one arm around his neck and another around his waist. Rory heard Jess singing the last few lyrics of the song to himself and smiled, wrapping herself tighter around him. Her brain felt a little cloudy and her body felt weightless, but it was a welcome feeling from the chaos that had inhabited her lately. This wasn’t quite like spring break where everyone around her was at an out of control state she couldn’t handle, this bar was full of people clearly in love with the same style of music as she was. 

Jess nuzzled his face into her neck and kissed her softly. His hands roamed, going from her waist down to her hips pulling her against him tightly. She reciprocated eagerly, lifting his head from her neck and kissing him softly and leaning against the wall so they could be with each other fully without fear of falling over. His mouth opened and Rory boldly explored his mouth with her tongue. Jess groaned but the sound of his approval was lost in the loud bass. They frantically carried on against the wall for a few minutes, not able to get closer to each other despite how much they wanted to. Jess reached down to the hem of Rory’s dress (he loved how many dresses she seemed to wear when she was around him) slowly brushed his hands up to her panties to see she was already wet. Rory’s mouth opened at the contact and her eyes popped open, immediately looking around to see if anyone had noticed and was disgusted by their interaction. Everyone around them seemed to be absorbed in their own fun, dancing, talking, and making out themselves. 

Jess trailed kisses up her neck to her ear to talk clearly enough for her to hear. “Do you like this?” he asked as he reached under her panties to play with her outer lips. 

Rory gasped and her eyes fell closed again. “I don’t…I don’t know,” she said in his own ear. Jess smirked and continued fingering her, reaching her clit and pushing against it. Rory whimpered and held on tighter to Jess. He continued his ministrations for several minutes until Rory felt a pleasant shudder come over her whole body and she let out one last groan against Jess’s neck. 

Jess took her lips again in a hard quick kiss and gathered her up in his arms tighter. “Let’s go somewhere, I need you now. “

Rory shook her head. “Can’t we just go back to your apartment?”

“I can’t wait. Want you too much. God I remember how fucking tight you felt it was so good Ror. Let’s go outside.”

She looked into his wild eyes and was entranced by how frantic and out of control he seemed to be. “You have…stuff right?”

“Stocked up on the way home,” he smirked. 

She sputtered in disbelief. “Really looking to get lucky huh?”

“Sure am,” he quipped.

She laughed and he took her hand and led them out to the back of the bar. They went out a back door into the humid night air and were ensconced in darkness. The only thing showing them the way was a stray light in the alleyway they were in. Jess immediately took her lips again, grinning against them as he backed them up against the smooth concrete wall of the back of the bar. She let her body take over, forgetting for a moment that they were in public and in fear of getting caught by someone. It was like their first time at the lake-illicit and forbidden but without inhibitions and totally free. Being with Jess was the opposite of her careful personality. It bought into the aspects of herself that her mother tried to bring out-playful, spontaneous, and fun. 

He reached again for her panties and took them off. She stepped out of them without looking, unable to stop kissing him. She didn’t feel his hands on her, but she heard the zipper of his jeans come down and his button go off. She heard the ripping of plastic and her heart rate quickened again when she opened her eyes and saw him carefully putting a condom on. He finally returned his hands to her body, lifting her up into his arms and she automatically wrapped her legs around his waist. 

His dick pressed against her wetness and she broke their kiss, panting quickly to catch her breath in anticipation. He slowly entered her and it was torture until he was full to the hilt. Her body took over and she grinded her hips down on his, groaning at the friction of his jeans against her skin.

“God damn you’re so tight Rory,” he groaned. 

She moaned at his words and met him thrust for thrust, loving how roughly his hands clenched her skin. It would probably leave bruises and under other circumstances it would feel painful but it felt beyond good right now knowing how much he wanted her. 

“I thought about this all day. God I would have fucked you so hard this morning if I had a condom,” he whispered in her ear. “But tasting you like that was just as good. How many times did you come Rory? Three? Was that a record? God I almost lost control. You make me lose it.”

Rory’s mouth opened for a loud keening noise while Jess used one of his hands to rub her clit to completion. She opened her eyes, the sensations running through her body made every nerve come alive. She met Jess’s eyes and they panted and looked in each others eyes as Rory went over the edge holding back a scream. Jess pumped in and out of Rory frantically at this point, pushing her into the wall roughly and the two groaned when Jess finally came to completion with a long sigh.

The two of them stayed in their position for a few minutes, catching their breath and coming down from their highs. Jess gently kissed her forehead and her cheeks and whispered against them how good that was. She sighed and hugged him tightly, not wanting to let him go.

She couldn’t believe she’d done that, again. But his entire being made her go crazy and it seemed to be the same for him as well. He wouldn’t have been able to wait the few blocks it took to get home and all her inhibitions couldn’t stop her from letting him fuck her in an alleyway. It felt dangerous but the way he held her? She knew she was safe. He wouldn’t have dropped her, he would have shielded and protected her if anything bad happened. Maybe it was because of his older age and clearer maturity and wisdom, but she already felt like this 24 hour trip was changing her entire being in all the good ways. She might really like Philadelphia after all.


	9. Chapter 9

The next morning found Rory and Jess tangled up in each other, peacefully in and out of sleep. Rory didn’t feel completely hungover but had a slight headache she was definitely fine sleeping off for a few extra hours. Jess had also been relentless for half the night, keeping her up once they got back from the bar with multiple rounds of sex. She was sore all over, using muscles she didn’t know she had, but she couldn’t say that she hated it. Her sexual relationship with Jess was new but from learning what he liked she was learning what she liked and needed as well.

She loved the pressure of his hands on her skin, the harder the better. They didn’t even have to be having sex. Even now as they lay there, one hand was wrapped around her hips, pressing his hand against her skin. It was a reminder that he was there and present with her. His hands on her skin always brought warmth to her body that tingled and lingered when she was near him.

“I don’t want to get up,” she murmured in his neck. His chest rumbled with a short laugh.

“We don’t have to. It’s Saturday. Day of rest.”

“That’s Sunday!”

“What if I was Jewish? It would be Saturday for me.”

“But you’re not!”

“How do you know?”

She faltered. He smirked. 

“Just kidding, I’m not,” he admitted. She smacked him lightly in annoyance. 

“You clearly just like to argue,” she pouted. He placed a kiss on her head and she smiled, burrowing into his embrace further. 

“Kind of fun to see you get riled up honestly. It’s cute.”

Her grin grew and she closed her eyes, breathing lightly in relaxation. The two of them lay there for a few minutes in silence, each deciding if this would be the moment they got up and broke the spell of their little bubble. Rory peeked an eye open though and took a look at how relaxed Jess was. 

“Hey,” she whispered. “Tell me something I don’t know about you.”

Jess didn’t open his eyes at her question, and he didn’t answer her right away. Silence hung in the air between them for a minute and Rory worried that she’d crossed some invisible line between them when it came to revealing things about themselves. She had bore a lot of her self to him over the past couple days, but the same couldn’t be said for him and she was starting to notice that. 

“I didn’t finish high school,” he admitted. Rory’s eyebrows raised in surprise. She didn’t say anything in response, hoping that he would continue with an explanation. 

“I lived in New York with my mom and it wasn’t the greatest. She just…she was flaky. Drank a lot, smoke a bunch of pot, had a bunch of boyfriends. It sounds like a big cliché story when you think about it to be honest. I hated school and spent more time in Washington Square Park reading than in class writing essays on things I already new. It just wasn’t interesting to me and Liz didn’t notice anything like that. It was incredibly easy to live life the way I was living but it was…lonely sometimes. I never had a full grasp on who I was, and I wanted to figure it out even if it felt lame at the time. I couldn’t admit back then though. But sometime before I turned 18 Liz had mentioned to me during a bad argument that I was just like my dad and I should just go off to California to be a beach bum like he was. I’d never met my dad, he left after meeting me in the hospital. So how could I be anything like this guy, this coward that couldn’t face his responsibility to me? So when I turned 18 I left to found out. There wasn’t a point to me graduating high school at that point.”

Rory absorbed and processed his story. She couldn’t help but wonder how hard it must have been to have that kind of life, to rely only on yourself and not know everything about where you come from. She and her dad were not the closest, but at least she could say he didn’t completely abandon his responsibilities towards her. He showed up sometimes and even if he didn’t show it correctly all the time, he did love her. 

“Did your mom have you young?” she asked.

“Yeah…might have been 18 or so, I can’t remember at the moment.”

“Hm…so did my mom.”

“I figured. I thought she looked too young to be a mom when I first met you guys.”

“She was 16. My grandparents come from high society so it was a big scandal when she got pregnant and had me. She refused to marry my dad and felt pressured still living with my parents so she ran away and ended up at Stars Hollow in the shed that I showed you. And then she raised me all on her own.”

“Very strong. Total opposite of Liz,” he noted. 

“Definitely came from two very different single mothers,” she mused. “Think we would have turned out the same if our lives were switched?”

“Well that’s a very nature vs nurture question. I don’t know. I do know that my life forced me to figure everything out on my own. I never had anyone to tell me how to live my life, how well I was doing the things I was good at. My self-esteem was never constructed by anyone else. And I did stupid shit when I was younger-got into fights, pulled petty crime like pranks. But eventually something had to give and I had to figure that out.”

Rory nodded against his chest. “I’m really glad you did. That takes a lot of tenacity when you only have yourself. I’ve never doubted that my mom would be there and support me through every goal I have.”

“I think writing the book helped. I wrote that in California.”

“Really?” Rory marveled. “Please don’t tell me you wrote it on the beach.”

Jess grimaced. “Could you tell?”

“Well I can see it now that I know! The flow of Jet’s big monologue at the end reminded me of big ocean waves in a weird way. Like totally natural but also visceral and potentially destructive.”

“That’s quite the visual.”

“Well you’re quite the writer,” she complimented.

Jess sighed. “Not lately.”

Rory looked up at him in concern. “Writers block?”

He shrugged. “A bit. I keep trying but it’s just not flowing all the way right. I was on a roll but it’s stalling.”

“You probably shouldn’t be spending so much time with me, see I’m totally distracting,” she cried.

“No you’re not, you’ve only been here a couple days that’s not quite the writer’s drought,” he rolled his eyes.

Rory giggled. “Ok I guess you’re right.”

His hands lifted her chin so that he could look her in the eye. “You’re a welcome distraction,” he assured her. He leaned down to give her a soft quick kiss. 

“Thanks for telling me all of that,” Rory told him.

Jess shrugged. “Easier to talk about now than it was when I was 18.”

“I bet you were an angsty emo nightmare when you were 18.”

“Oh you would have hated me! The book reading is the only thing you would have liked about me!” he lamented.

She laughed and kissed his neck affectionately. “I think I would have seen past it. I think I would have seen your heart a bit.” 

Rory is sure she would have been fascinated with him at any stage of his life.  
****  
A couple weeks in Philadelphia goes by and Jess finds that his regularly scheduled life has to go back to normal, but that means something else for him and Rory.

A pattern begins to form for the two of them. They don’t talk about it, but his long hours at Truncheon and wherever else he goes leaves her feeling weirdly insecure, especially because she doesn’t always know where he is and what they’re doing. 

She goes with him to Truncheon a couple times, just to get out of the house but it ends up with her in the corner keeping busy by reading books and reorganizing the shelves. Jess is busy with meetings and finishing up editing deadlines so there’s no time for him to entertain her. It’s fine, because Matt and Chris are friendly and come check on her throughout the day. She wanders around aimlessly at one point during the afternoon and observes the three boys arguing over a problem with the layout of the zine. 

“I don’t know what’s wrong with the program,” Matt says frustrated. “I knew we shouldn’t have switched to this one but you said it would be faster Chris. It can’t be faster if I don’t get how to use it!”

“I mean I told you should read the manual. You can’t complain now that everything is due tomorrow,” Chris points out.

Matt rolls his eyes and Jess tries to mediate the situation.

“Look you just need to put this one article and picture in here and you’re pretty much done. Just look through the manual and see if it’ll give you an answer!”

Rory cuts in, seeing the software disc and recognizing the program they’re using from her time with the Yale Daily News. “Let me see the computer. We use this program at the Yale Daily News, I’ve watched the layout editor do everything before.”

The boys looked at her skeptically but nodded and let her behind the computer. Rory looked at what she was working with for a minute before clicking and moving a few things around. Matt, Chris, and Jess looked amazed as Rory fixed the layout for the page they’d had so many problems with in a few minutes.

“How did you do that?” Chris asked.

Rory shrugged. “Our layout editor has had the same problem a couple times, it just takes changing a few settings around. All good?”

The boys nodded dumbfounded and Rory went off happily to continue reading a new book, glad that she was useful for a small amount of time that day.

Other days Rory stays around in the apartment while Jess goes to work. Sometimes he doesn’t come back to the apartment until almost 9 and she spends the whole day anxiously cleaning and rearranging his book collection. She expected him to text or call if he was going to be late, but she doesn’t hear from him. The days he does manage to come earlier by 6 or 7 he’ll take her out to a fun restaurant and they’ll walk around the neighborhood. They’d had a fun time walking around the Italian Market one night and Jess promised to bring her back on a weekend when they could shop for food and hang out in the sun. She doesn’t like to go out and explore without him during the day though. The couple times she’d wandered around by herself had been anxiety inducing and she didn’t want a repeat of that feeling. 

So she stayed in the apartment. All day, every day she found something to do, something to read, something to watch on TV to spare some time until Jess decided he wanted to make a plan on what they would do that afternoon/evening. She wasn’t sure how hard to press. After all, Dean had always been responsive by calling and making plans with her all the time. It had been an easy relationship. With Jess, she still wasn’t sure how she was supposed to approach him all the time. She didn’t want to pressure him into spending time with her just because she was visiting and staying with him. She understood that he had responsibilities and a life that existed before she got here, but if he had a guest wasn’t he supposed to call?

It wasn’t until Friday that she broke. It was almost 1 and she was going stir crazy in the apartment. She had enough money to get a cab if she needed to, but she needed to find something to do. She got on her laptop and did a search of fun things to do in Philadelphia. Major monuments, bookstores, and coffee shops. From a list she looked through, she finally saw something that piqued her interest. She had forgotten that University of Pennsylvania was located in Philadelphia. She applied there when she initially sent out applications but didn’t think much about it when she didn’t get accepted. She got into Harvard, Yale and Princeton so the big three was cushion enough to soften the blow of that rejection. It was an Ivy League school and seemed interesting when she initially applied to go there but she didn’t go further in her research of it. 

It could be interesting to spend time on a college campus, somewhere she felt at home. Even though she didn’t end up going to Harvard, she’d felt it was a natural fit to be on those grounds where all the knowledge she could soak up was just waiting for her when she went to visit with her mom during their runaway bride trip. And despite the insecurities she had at Yale, everything about the campus was everything she wanted out of a school. Maybe she would find some peace at this school, if even for an afternoon.

Rory packed up some books and her essential items and headed out the door. She was able to find a cab pretty quickly and gave the man an address she found for a building on the campus. Her cab ride to the campus was a quiet opportunity for her to observe more about the city, she spanned neighborhoods and saw the incredibly different cultures that faced her from the car. Every time she took the time to observe the city she found herself becoming more interested in figuring it out. 

When the cab dropped her off at a busy corner, Rory took a look around. It didn’t look that different from the rest of the city but Rory saw a concrete walkway path across the street from her that led to more lush green grass surroundings. Rory followed it curiously, making sure to check for stop lights so she didn’t get run over. As she followed the path she took notice of the sign that signaled that she was on the campus and that this was Locust Walk. She’d briefly read that this was the main walk of the campus where most major buildings could be found. She saw two big buildings immediately that seemed to be a campus building and a library. She furrowed her eyebrows though when she saw that in front of the library was a sculpture of a broken button. Small children ran around, crawled under, and climbed on the realistic button laughing as their parents stood around casually talking.

But when she looked to her left she was faced with an incredible sight. A statue of Benjamin Franklin stared her down in front of an expansive green lawn that led to a gothic style building. The bricks that composed the building were green in its color and while that would seem obnoxious in other cases it was incredibly majestic in this case. Rory walked towards the building in wonder and looked around for any kind of sign to find out what this was and all its history. She finally found a sign that told her this was College Hall and the oldest building on campus. The small anecdote continued to tell her that the building may have been the inspiration for the house seen in The Addams Family and her mind clicked as to why the building was familiar to her. She smiled, deciding that this is where she was going to spend her day.

She found a tree on the lawn settle down in, hoping it was just as comfortable as the tree she loved at Yale. It wasn’t the same but it was good enough for some casual reading. The grass felt cool against her skin and she sprawled on the ground not needing to worry about modesty since she decided to wear shorts for once. She opened up her book and put on her sunglasses, engrossing herself in another world for a couple hours. She fell asleep at some point, her book on her chest, the shade hiding her fair skin from the hot sun. She was content and peaceful.

Rory’s eyes popped open and struggled to see clearly against the brightness of the sun. There was a foot nudging her legs to alert her of their presence and she tilted her head until she saw two figures standing in front of her. Because of how bright the sun was, she couldn’t quite make out their features but they stood there expectantly as if they were waiting for something.

“Miss you do you have 89 cents?” a man with a high voice asked her. She frowned and her brain clicked knowing that phrase sounded familiar to her. 

“Um,” she hesitated. “No I don’t?”

“Are you sure? Because you’ve been sleeping so you might not know,” the man argued. She was able to make out that there was a woman with short hair next to him waiting as well. Rory had never encountered someone asking her for money before, so she was not sure at all how to handle this. She definitely didn’t have change on her though.

“I’m really sorry sir, I really don’t have it on me,” she pleaded.

“Well anything will do! But 89 cents would be great!”

“Hey! Ralph!” she heard a voice call out in the distance. “Stop waking people up. No one has 89 cents!”

The man looked over to the passerby with an exasperated look. “You never know!”

“No Ralph, you ask everyone all the time and no one has 89 cents. Try asking for 25, 10, even a dollar! Come on, here’s a couple quarters. Leave this poor girl alone.” Rory looked to see a girl walk up to them holding out change for the man and his female companion to take. Ralph took it eagerly and smiled gratefully to the girl. With a thank you they walked off and didn’t take a second glance at Rory.

Now that her vision had cleared, Rory looked to her savior and saw a tall girl with dark chocolate skin. She had big brown eyes and her hair was wild with natural frizzy curls. She’d never felt the need to describe a woman’s lips as luscious but she supposed the occasion called for it this time. The girl would easily stand out in a crowd in her long tangerine dress that made her skin glow in the sun. Rory was almost jealous at how natural summer looked on this girl as opposed to her with her fair skin that had to hide away. 

“I hope they didn’t bother you too much,” the girl said. “I saw them wake you up and start asking questions. Usually they leave people sleeping or with headphones on alone but he must have been desperate today. Sucks.”

“Oh, it’s ok I guess. It’s probably good they woke me up before I burned to a crisp. Thanks for stepping in though, I really didn’t have any change on me.”

The girl shrugged. “No problem! And you don’t look worse for the wear. This is a pretty good tree to hide under.”

Rory smiled and sat up properly. “Yeah this is beautiful, I can’t imagine how the people who come here get anything done when they have to go to class. I’d stay here all day.”

“Oh you don’t go here?” the girl asked confused. 

Rory shook her head. “No just visiting and…curious I guess.”

“Huh. Have you seen the rest of the campus?”

“Not yet. I saw this and it’s as far as I got.”

“Well you should definitely see it all. I’m biased but this is the greatest place,” the girl gushed. Rory grinned at her enthusiasm. 

“I’m Rory by the way,” she introduced, bringing her hand out for the girl to shake. 

The girl brought her own hand to Rory’s, meeting in a firm shake. “Nice to meet you! I’m Ama.”

Rory’s eyebrows furrowed. “I’ve never heard that kind of name before.”

Ama laughed. “Well I’ve never met a girl named Rory before, it’s usually a boy’s name.”

“Touche.”

The two girls laughed. Rory looked around nervously noticing the lull in conversation. Making friends and small talk with new people wasn’t always the easiest for her and she was finding it hard to think of a next step in this interaction. But it was also hard to think about how to get out of it. 

Ama did her a solid and found a way to make it work. “Hey so since you’re visiting I could show you the best coffee place on campus? As long as you don’t have to be anywhere. It’ll definitely save you from any Ralph types.”

Rory giggled. “Oh I definitely need saving. And I definitely never say no to coffee.”

Rory got up and collected her things, conversing easily now with Ama after she took notice of the book Rory was reading. She was pleased to see that Ama recognized it and they talked about the plot points as they walked down the rest of the pathway Rory hadn’t gotten to. Noticing Rory’s amazed face, Ama took the opportunity to play tour guide, slowly pointing out the different buildings that surrounded Locust Walk and small facts about their functions. Rory was impressed that such a campus could exist in this vast city. She almost didn’t feel like she was in Philadelphia. Penn definitely existed in its own nook in the corner of the city.

Rory and Ama reached a busy street and crossed over to their destination, a small coffee shop called Hub Bub. 

“This place started out as a coffee truck actually,” Ama explained. “The guy who started it is an alum and he would park at different corners of campus everyday selling his coffee. It got so big that he had enough attention to open a storefront.

“That’s amazing!” Rory exclaimed. “God I’d follow that truck around everywhere. It would be my religion.”

“He’s not bad looking either,” Ama teased. “It makes getting the coffee ten times better.”

“Delivery and barista cuteness are an important factor of deciding if a restaurant or coffee shop is worth going to. My mom taught me that.”

“I have to agree with your mom, I’m pretty sure knowing how to make a good cup of coffee is top 5 in my list of essential life partner qualities,” Ama agreed.

“Yeah my mom just started dating the diner owner in our town that has the best coffee in the world. We’ve been going to him for years. It probably should have happened a long time ago.”

“That’s a good catch!”

Rory nodded with a smile and girls went up to the counter and ordered their coffees. They sat down at a rustic wood table with charming red chairs once they received their orders and quietly took sips. Rory sighed dreamily at how rich the coffee was. 

“This is amazing,” she gushed. “Almost as good as Luke’s at home!”

“They have a location downtown in Center City too if you need another fix later. You staying in the city long?”

“No…well…actually I don’t know.”

“You don’t know?”

“Well I’m kind of here visiting someone but we didn’t decide how long I’m staying…or much of anything really.”

Ama’s eyebrows furrowed. “Ok I’m confused.”

“Me too!”

“But it’s your story?”

“My life has gotten pretty confusing over the past month or so, it never used to be like this. I never used to be like this,” Rory worried.

“Like what?”

“A basketcase!”

Ama gave her coffee companion an eye roll and took a sip of her coffee. “Ok you need to take a moment because your anxiety is rolling off you in waves and it’s making me dizzy. How about we start small. Where are you from?”

“Stars Hollow. It’s a really small town in Connecticut,” Rory sheepishly answered, embarrassed by how much of a fool of herself she was making. “What about you? You still haven’t told me where your name is from? I don’t recognize it.”

“Well my name is from Ghana. My parents grew up there but I was raised here in the States. They gave me the name Ama because I was born on a Saturday, it’s how naming works there.”

“Oh wow, that’s beautiful! I don’t think I know many people from Africa,” Rory told her honestly.

“Really? Not many of us in Stars Hollow huh?”

“No…when I think about it…it’s pretty white. My best friend is Asian but she’s a bit of an anamoly in our town.”

Ama nodded and took another sip of her coffee. “So what exactly brings you to Philadelphia? Did you want to transfer to Penn or something? You seemed pretty fascinated with the campus.”

Rory sputtered, “I mean I am but no…no I go to Yale actually. And I love Yale, it’s a great school and close enough to home. I’m just here visiting a friend…I guess he’s my friend. I’m not sure what to call him-“

“Oh is he a fuck buddy or something?” Ama asked bluntly.

“What?” Rory recoiled.

“You’re not calling him your boyfriend but you’re also not sure whether to call him your friend,” Ama pointed out.

“That doesn’t mean we have to call him my fuck buddy,” Rory hissed quietly so that surrounding customers wouldn’t hear their conversation.

Ama laughed. “I mean it’s ok if he is, more power to you. Unless you want him to be your boyfriend and not your…sex friend,” she corrected. 

“I’m not really sure…I don’t know what we’re doing. I mean I came to visit him on a whim after we spent one night together and he seems to want me here? But he’s also not much of a planner. He’ll leave me for whole days without saying anything or making a plan like ‘Hey what do you want to do for dinner’ or if I want to go see a movie or do anything fun. He’s super busy with work and I get that but…just tell me something! I can’t be that girl sitting by the phone,” Rory rambled. She stopped when she saw Ama’s amused expression and mumbled an apology for once again going off on a tangent.

“Sounds like he’s stringing you along a bit,” Ama observed. 

“No!” Rory defended. “He’s not. When we’re together it’s…really great. I’ve never met anyone like him. But I don’t know how to approach him because I’ve never met anyone like him. I only ever had one boyfriend and he was so nice and always called and made plans and was super reliable.”

“But this guy isn’t your first boyfriend,” Ama pointed out. “He’s his own person. Comparing the two will get you nowhere. Maybe you didn’t have to ask for what you wanted with your last boyfriend but you may have to now with this guy if you want to get what you want.”

Rory pondered that, thinking back ironically to Jess’s sexual style. The way he always asked her what she wanted during sex seemed strange to her but in a way she recognized that he wanted to know what her desires were. She’d been unable to voice them during sex and it seemed like she was still unable to outside of the bedroom.

“That’s actually really helpful advice. Thank you,” Rory said sincerely. 

Ama shrugged. “No problem. It’s kind of what I do.”

“God I must sound crazy, here I am rambling about my problems and I still don’t know much about you,” Rory said. “I’m guessing you go here to Penn? What do you major in?”

Ama laughed. “I’m about to be a junior actually. I’m majoring in urban studies but I’m minoring in fine arts. Hoping to merge the two in a lot of ways. My dream is to use art to really revitalize communities I guess. I haven’t figured it all out yet but I have time.”

Rory marveled at how relaxed Ama was for going into her junior year. Even as a sophomore Rory fretted over her career trajectory and how all her classes would contribute to those end goals. Not knowing what to do scared the hell out of her. 

“Aren’t you worried about figuring it out though?” Rory asked uncertainly. It seemed like a big question to ask someone she didn’t know very well but it was forefront in her mind.

Ama shrugged. “Not really actually. I’m in a good place. This campus and university is amazing and I’ll take the opportunities I can get but I don’t have to know exactly what I want to do come graduation day. Most people around here are like that and it’s intimidating but more often than not you just find a bunch of nerds who love to learn and also love to party.”

“Really? That’s not at all like Yale.”

“We’re definitely the party Ivy. Work hard, play hard around here, especially when the city is your playground.”

Rory gave her a small smile and tried to dampen down the gnawing feeling of jealously that bubbled in her stomach. Here was this girl in a similar position as her at a great school and she wasn’t half as stressed as Rory seemed to be. Was it just her? Was there something wrong with Rory?

The vibration of her phone interrupted her thoughts and the conversation and Rory looked to see that Jess was calling her. Her eyebrows rose in surprise and she mumbled a quick sorry to Ama before answering the phone. 

“Hey,” she answered.

“Hey where are you?” Jess asked curiously.

“I’m in West Philadelphia but not born and raised,” Rory quipped.

“Wait what? Where in West Philadelphia?”

“University of Pennsylvania?”

“Oh,” Jess relaxed. “Ok. Not all parts of West Philadelphia are super safe. I got worried. That was a corny joke though.”

“I’ve got puns all day bud,” Rory quipped back. She saw Ama laugh at her end of the conversation. 

“Well are you coming back soon? I got done earlier than I thought I would. Got us tickets to see The Distillers, one of the poets who comes through had a couple extra.”

Rory almost rolled her eyes. “Sure, I’ll be back soon. I think I made a new friend actually and we’re having coffee so I’ll take a cab back when I’m done.”

“Ok,” he replied easily. “I’ll see you soon then, I don’t think the show starts until 9.”

The two said their goodbyes and got off the phone. Rory bit her lip in deep thought and Ama looked on in interest. 

“I guess I have to go soon, he got us tickets to see The Distillers,” she told her. 

“That’s cool! That sounds like a fun plan!” Ama encouraged. “That’s what you wanted right?”

“Yeah but it’s always at the end of day, spontaneous and like I have to wait around for him to decide what he wants. I don’t know, I either need something to do around here or I’m just going to spend the whole summer waiting on some guy to come up for air from his busy work life to notice me. I really can’t blame him too much, he helps run a publishing house and bookstore and is trying to write a new novel. I knew this when I came here!”

“Well hey, despite your rambling you seem to be kind of cool Rory so if you get bored, we can hang out,” Ama says. “I’m taking a class a couple days a week but other than that I’m free.”

“Really?” Rory asks meekly. “I’m usually much more fun than this I swear!”

“I can tell. You’re funny!”

Rory smiles and takes one last sip of her coffee. “I appreciate that. I could always use another friend, especially right now.” Usually in these times of uncertainty she had Lane to turn to, but she was far away in Connecticut with her own problems. They’d talked a few times in the past couple weeks but it wasn’t the same. Besides, maybe this would give her something else to do outside of the apartment that wasn’t by herself.

The girls exchanged numbers, Ama telling her about this exhibit at the art museum that they could maybe go see in a few days. Rory agreed eagerly and they discussed the best day to go as they gathered their things. They walked out back outside to the slowly setting sun and said their goodbyes.

“I’m glad I met you today,” Rory thanked Ama. “I’m sorry for all my rambling I’ll keep it down next time.”

Ama waved her off, “I’m glad I met you too! I always like making new friends. And maybe next time I’ll unload my shit on you.” She winked.

Rory giggled and waved goodbye as they went their separate ways. The smile stayed on her face as she got in the cab and made her way back to Jess’s. At least she wouldn’t be over the top annoyed when she got back to him, but she went with a renewed confidence.  
***  
Rory walked into the apartment and found a couple lamps on paired with the sunset to give the living room a romantic glow. There was Chinese food on the table with plates and forks already set up. She saw Jess come out of his room with wet hair wearing a white tshirt and black jeans. His staple. She let her eyes wander over his body satisfied with how tight the shirt was and how it showed off his lean muscles.

“Hey you’re just in time,” he walked to her with a smile and took her in his arms to give her a deep welcoming kiss. She melted into it easily and despite how restless and annoyed she had been during the day she couldn’t deny that Jess was attentive to her when they were together. He couldn’t help that he had a life. He broke the kiss and led her over to the couch to sit and eat. Rory rested against him and ate dumplings, listening to him talk about his day and new author he landed today. When a lull in conversation came up Rory mentioned her adventure for the day.

“I made a new friend!” she told him proudly. “She saved me from the 89 cent guy. He found me!”

Jess guffawed. “Stop you met him!?”

“I didn’t have any change though, I felt really bad. But Ama saw him and came to shoo him off with some quarters she had. Then she showed me around the campus and we got coffee. It’s pretty up there.”

Jess agreed. “Yeah Penn is a cool campus for sure. It’s so weird how you don’t even feel like you’re in the city when you’re there.”

“That’s how I felt too! They have this beautiful library too, Ama told me it’s the fine arts library. I’ll have to check it out.”

“I’ll go with you, I’ve seen it before too.” Rory smiled at him and agreed, happy that they were finding something else to do together. It reminded her of the conversation she had with Ama earlier. Rory took a deep breath and turned to look at Jess fully.

“So…you’ve been super busy lately right? Do you want me to go back to Stars Hollow?”

Jess frowned. “Why would you think that, of course I don’t want you to go. Do you want to go?”

“No! I like being here and spending time with you. We have a lot of fun and you’ve shown me so many cool things around the city but I don’t really know what I’m doing here. I kind of sit around all day waiting for you to be free, not knowing what we’re going to do that night or the next day. I’m a girl that like plans and having a purpose and I just don’t have that right now. It’s weird.”

Jess listened to her pensively and nodded when she was done talking. “Ok.”

“Ok?”

“I get what you’re saying, I just wish you would have said something earlier. I’m sorry I’ve been so busy. And you could explore things on your own like you did today you know?”

“I know but I’m just not always good at exploring new things by myself. I’m surprised I even went to Penn today!” she cried. 

“I have a thought. Matt and Chris mentioned it to me today actually and I agreed with them.”

“Oh?”

“Matt hates doing a lot of the zine stuff by himself, especially the layout. He’s still talking about how you managed to fix his problem in 5 minutes last week. How about you intern for us this summer and help with the zine? We’re starting to put it out bi weekly so it’s busier than usual. We can’t pay you anything but it’s something to do and you have the experience.”

Rory’s eyes lit up. “Really? Are you sure?”

“Yeah we’d love to have you. From what you told me about your work on the Yale Daily News it would be a similar thing. Some book reviews, interviewing local talent in the city. Matt will be able to tell you more about it.”

“Why didn’t you tell me about this when I first came in?”

“I thought it would be even better once you’d had some dumplings!” he laughed.

Rory hugged him with an excited squeal and Jess hugged her back with an easy smile. “This is going to be so great! Thank you, thank you!”

“You don’t have to thank me, we wouldn’t offer it to you if we didn’t think you couldn’t do it.”

Rory sighed with happiness, surprised by how easily their problems had been solved. She went back to eating her dumplings with a shit-eating grin.

“By the way,” Jess started. “Next time you’re worried about something just tell me ok? You’ve gotta tell me what you want or else I’m not gonna know.”

Rory’s grin slipped a little and she swallowed her dumplings with a hard gulp. “You’re right. I’ll be better about that. I’m just not always good at this communication thing. It was really easy with Dean but…you’re not Dean and I have to remember that.”

“I’m definitely not,” Jess agreed. He watched Rory quietly take another bite of her food and took her free hand in his giving it a squeeze.

“Hey I hope you remember that I’m really glad you’re here and I’m having a lot of fun with you,” he told her with a wide smile.

Rory returned the smile. “I’m having a lot of fun with you too.”

Jess kissed her cheek and got up to throw away the food on his plate and wash his dish. Rory watched him go and smirked when she saw he was wearing the black jeans that made his butt look really nice. It made her think of her mom and Sookie and how they always made funny comments about guy’s butts. She missed them.

She finished her food quickly and got up to get dressed for the show tonight. She took her plate to Jess and placed it in the sink and wrapped her arms around his waist from behind. She kissed the back of his neck and whispered in his ear. 

“I am going to keep thanking you because this is going to be so fun and make this summer even better. You’re great.”

Jess snorted. “Just get dressed Gilmore. We’ve gotta celebrate,” he winked.

She blushed already catching onto his double entendre. Sex wasn’t all he thought about but things were always so intense and good when they were together that they couldn’t help but get tangled up in each other every chance they got. Rory gave his neck one last kiss and hurried off to his room to get ready. She picked out the most colorful dress in her wardrobe and took extra care to shower and get ready. 

This was a celebration after all. The prospects of her summer had become even more productive in the matter of a day with a new friend and a new job.

**Notes for the Chapter:**

> This got unusually long but I was so excited to introduce you all to Ama. Like the original series I think it's incredibly important for Rory to have more female friends, especially those that give her perspective. I think Ama will play that role. When I think of her, I think of Jerrika Hinton actually so let that give you a good picture! Hope you enjoyed!


	10. Chapter 10

**Notes for the Chapter:**

> A/N: Two chapters in one weekend is really quite a feat for me. I hope you all don’t get used to this but winter makes me hibernate anyway. Might as well write!

Since Rory and Jess had started sleeping together, literally and figuratively, they’d taken to having morning conversations. It became a ritual to start their day, each taking unspoken turns to ask the other a question. They never made rules about what they could ask or how honest they had to be, they just fell into it. Sometimes it would be something silly like Rory asking Jess why he used so much gel in his hair. Or it would be something serious like Jess asking Rory questions about her mom. Jess almost didn’t like to admit it, but it was becoming his favorite part of the day, more important than going to work, eating dinner, or having sex with her. They built a cocoon in his bed, a safe haven and place where they promised not to judge each other for what was said in between the sheets in those moments. This morning it was Rory’s turn.

“How many girlfriends have you had?” she asked playing with his fingers. They lay across from each other this morning, heads on their own pillows but their fingers intertwined. She rubbed her thumb over his knuckles, enjoying the softness of his skin in that spot in opposition to how rough his hands felt.

“One,” he answered easily.

“Would you tell me about her?” Rory continued after Jess didn’t elaborate further.

“It was in high school and her name was Molly. She was sweet, very earnest. She wasn’t my first time, I’d already lost my virginity by that point so it wasn’t some heart eyes first love first everything relationship like it was for you with Dean. I wasn’t her first either. I remember she used to try to make me go to school sometimes when my slacking off in that department reached its peak. I would only go to hang out with her honestly. She was really good at math but hated English and literature. I tried our whole relationship to get her to read one book but it never took,” he told Rory with a wistful look in his eye.

Rory took notice. “How did it end?”

“I left to go to California. She was staying in New York, had dreams and was applying to a couple schools in the northeast and Midwest. It was never going to be the great love of our lives. She was a good friend most of all and she understood what I had to do for myself. She didn’t like that I wasn’t graduating but she made me promise I’d get my GED at some point. We didn’t keep in touch but I did keep my promise.”

Rory smiled at that fact. “So how come no more girlfriends after that? You’re 23 I would think girls come flocking to you.”

“They do I guess but I just don’t do relationships.”

Rory’s body stiffened. “You don’t do relationships?” she clarified.

Jess took notice of how her hand had stopped playing with his own and read her body language. His face became concerned. “No Rory it’s not…I just…do you want me to be honest with you?” 

“What are we doing Jess?” she asked quietly. “I’ve been here for a few weeks and if I were to introduce you to someone like…Ama I wouldn’t know what to call you. She called you my fuck buddy at one point and it felt wrong, it felt dirty.”

“That’s not how I see you,” he assured her.

“Then how do you see me? What do you like about me?”

“You’re like a caged bird to me sometimes. You have beautiful deep thoughts about the world and literature that open up conversations I’ve never been able to have with other women. But you are so shy, so unsure of that part of yourself with me that your humility holds you back. You’re funny and witty, you’re curious but you let this anxiety eat that up. Women don’t keep my attention for very long Rory and it has more to with me than it is them. I don’t know how to break that barrier of being interested in a woman to making a commitment to them. But you’ve held my attention since I first saw you at Luke’s and it keeps growing. I don’t know how to label this, you have to give me time on that but I will say that I enjoy figuring you out and I think it’s going to take me a long time to do that.”

Rory stared at his hands pensively for a few minutes, processing his answer. “It’s not just sex for you,” she confirms.

“Oh don’t get me wrong the sex is fantastic, I clearly can’t get enough of you,” he smirks.

Rory blushes. “You’re ridiculous.”

“You know I’m right! You can’t get enough either, you jumped me when I came home two nights ago!”

“I did not jump you! I simply took your bag from you and led you back to your bedroom. Rest after work is important you know.”

“I wouldn’t call you riding me rest but sure.”

“You didn’t have to do much work!”

“Touche.”

The two glanced at each other and burst into laughter at their argument. She liked that she’d gotten comfortable enough to banter with him like this. It was still wrong to compare this thing with Jess to what she had with Dean, but it was Rory’s only real marker for how she was changing. She’d never joke like this with Dean but she couldn’t pinpoint whether that was on Dean’s inability to banter with her like this or Rory’s lack of confidence in making sexual overtures that could be used as banter later on. Either way Jess had caused a shift in her but it was creating a dynamic that put a smile on her face and gave her the power to put a smile on his.

“So what’s up for today?” Jess asked.

“Well Matt doesn’t need me today so I’m gonna meet up with Ama. Maybe get some lunch and sit in the park. I might stop by Truncheon after since I’ll be a few blocks away. You?”

“Have to finish up an edit for Blake’s manuscript today. I’ve been dragging on that. If I get that done in time I might go somewhere to write, maybe the Schuykill banks. Sitting by the water might help. So I won’t be at Truncheon if you come by later.”

“Still no luck with the writing?” Rory asked sympathetically.

Jess sighed frustrated. “It’s getting better but maybe being by a body of water will help a little. We’ll see. What do you want to do tonight?”

“Can we stay in? We’ve been on the go this week, it’s been fun but I need a break. Plus I promised Ama we’d meet up with her at First Friday tomorrow so might as well get a break now. Get a movie on your way back?”

“You know how this night will end if we stay in the apartment.”

“How is that any different from nights we go out? And who says I don’t want that?” she asked coyly.

A beat passed. “You’re right.”

Rory giggled and snuggled against Jess laying her head on his bare chest. She couldn’t pick an exact moment but sometime since their small argument and she started her internship at Truncheon a barrier had broken between them sexually. She wasn’t as afraid to admit that she wanted Jess as much as he wanted her. The only thing that was between them was Rory’s lack of confidence about pleasuring Jess. He could go down on her in any position all day long but she had no idea where to start with him. She gave Dean a handjob once but it had been so quick that she didn’t remember or know how well she did it. And she wanted to be good for Jess in every way. Thankfully he never said anything about it, never questioned it or pushed her into doing that for him.

“Hey how about we go see a movie? Give my window unit a break for once and hang out in an air conditioned theater,” Jess suggested. 

“I could do that. Can we sneak in snacks? Movie theater concessions are robbery.”

“Bring your big bag Gilmore.”

“Look up some times and text me the details?”

Jess leaned down and gave Rory a series of soft quick kisses. “Will do,” he murmured against her lips before giving her one last kiss. Rory smiled against his lips and sighed in contentment. Jess separated from her and immediately hopped up out of his bed in a rush.

“I need to go before you distract me all day!” he called out. Rory laughed and fell against the pillows, burrowing in them further and breathing Jess’s smell.  
****  
Rory and Ama sat on a bench in Rittenhouse Square that afternoon, eating gelato they’d picked up a few blocks away at Capogiro. When considering their lunch choices, both girls looked at each other and agreed that ice cream was probably a better option than anything else. Ama was quickly becoming a good friend to have around for Rory. She reminded her of many elements of Rory’s life back home in Connecticut and softened the blows of homesickness that sometimes plagued her. She had an eccentric fashion sense that reminded her of her mother, blunt and honest opinions like Paris, but a fun and calm spirit like Lane. She seemed to love her family fiercely and told Rory many a story about how strict and traditional her parents seemed to be. It was foreign to Rory but Ama took it in stride instead of rebelling against it.

“I don’t think I had been to a sleepover until I was 16 maybe?” Ama told Rory.

Rory’s eyes widened. “Really? Your parents were against sleepovers?”

Ama shrugged. “Any time I asked my mom would ask why my bed wasn’t good enough and why I would want to go sleep on the floor of someone else’s house.”

“That seems really lonely, I loved sleepovers as a kid,” Rory observed. 

“Maybe but I didn’t think I was missing anything in the end. It’s really funny now that I’m older and sure it was the end of the world back then but whatever.”

“Your mom is the total opposite of my mom clearly.”

“You don’t talk much about her. You only mention how she would like something we’re talking about or seeing. What’s she like?”

“She’s my best friend. She’s really fun, raised me on her own when she had me at 16. So she’s really strong. She just opened her own inn actually, it’s been her dream for a really long time. I miss her.”

“I’m sorry. I bet phone calls aren’t the same all the time, I know it’s not for me and my parents.”

“We haven’t talked on the phone much,” Rory corrects her sadly.

“Why?”

“She’s not very happy with me right now.”

“That’s surprising, I thought she was your best friend.”

“She is…but she’s not happy with some of my choices lately.”

“That sounds like more of a mom thing than a best friend thing then.”

“What?”

“Well moms aren’t supposed to be happy with the choices we make sometimes. Lord knows my mom isn’t. I lived by my parents rules when I grew up because I had enough respect for them and the values they gave me required that. But once I came here to college I had to live by my own rules. My mom didn’t like when I dyed my hair freshman year or that I minored in fine art. She wants me to be a lawyer or doctor but that’s because it’s her own values giving her that perspective. So I live my life and I don’t expect her to like every choice I make. Sometimes I just stay discreet and don’t tell her what I’m doing. That’s something my older brother never learned though so he gets angry when our mom nags him for all his choices.”

Rory continued to eat her gelato and pondered Ama’s explanation. “But I don’t want to hide things from her. I’ve never had to do that before, we’ve always been able to be open with each other for the most part.”

“Hey I don’t know what exactly your mom isn’t happy with, I’m sure you staying in Philadelphia with an older guy is a factor but it’s clear there are some things you can’t be open with her about if you want to get along. So either you need to change your tactics or she needs to get comfortable.”

Rory nodded. “You have a lot of good advice. You should have majored in Psychology.”

“That’s probably true, I’d actually get paid to listen to your problems huh?” Ama teased.

Rory blanched. “Oh no I’m doing it again aren’t I? Let’s stop talking about me, what’s going on with you? What problem do you have?”

“Honestly? Kind of horny these days, it’s been a big dry spell. And summer is totally meant for fun flings with fun boys.”

Rory coughed, swallowing her gelato down the wrong pipe. There was that blunt honesty. “Oh so you have that problem?”

“Sure do, and if I don’t do something about it soon I’ll have to live vicariously through you and your hot writer guy’s sex life.”

“Stop!”

“It’s true! Does he have any hot friends?”

“I don’t know if you would like Matt or Chris.”

“I don’t have to like them that much Rory.”

“Wow, this is a lot.”

“Hey I’m a woman with needs, this is exactly how guys do it and get away with it!”

“Ok so you need a guy…any guy?”

“Preferably attractive, can speak in full sentences, that sort of thing. Maybe we’ll meet someone at First Friday tomorrow night. You’re bringing writer boy right?”

“Why do you call him writer boy instead of Jess? That is his name you know.”

“I do but it’s more fun to give him a little code name,” Ama giggled. “Anyway we’ll definitely have to find me a man so that I’m not third wheeling with you two all night.”

“It won’t be like that! I want you to meet him!” Rory assured. “I feel like I’ve talked him up so much.”

“You have. How are things by the way? Gotten better on the planning and communication end?”

“Yeah he’s great,” Rory smiled. “I think he gets it now. You were right I just had to actually tell him what I wanted and then he adjusted. We talk about what we’re doing for the day usually in the morning and make a plan. Feels nice. And interning at Truncheon has been great so far. It’s nice because I’m working more with Matt and not Jess so we’re not spending every waking moment together. Oh by the way we’ll have to stop by this one gallery tomorrow because Matt wants me to do a story on the owner.”

Ama agreed easily, “Sounds good to me. Glad things are cool with you and writer boy by the way I’d hate for things to go sour so that you run away back to Connecticut.”

Rory scowled. “What an image.”

Ama laughed. “Sorry, I’m just saying!”

Rory rolled her eyes. “It’s fine, things are good. Although…I do have one question maybe you can help me with answering?”

“Shoot.”

“Um,” Rory started shyly. “The sex with us is amazing but I just…I don’t know what to do to please him. He does stuff for me all the time but I’ve never done that to a guy before. I don’t want to embarrass myself. I’m a bit of a perfectionist that way.”

“Ok so you mean giving him a blow job?”

“Ama!”

“That’s literally what you’re asking!”

“We’re sitting in a park and you’re talking loudly about blow jobs,” Rory whispered and ducked her head down.

“Ok so would talking about hand jobs be better? How about we give it a code name. Do you want to talk about giving Jess a hand?”

“That’s better I guess.”

“Ok well hand jobs are pretty hard to mess up. Start with that. Make sure your hand isn’t super dry, use what he’s got and tell him to tell you if you’re doing a good job or not. It’s much better when the guy directs you like if he says to go faster or slower.”

“He won’t have a problem doing that,” Rory muttered to herself.

“What?” 

“Nothing.”

“Ok,” Ama replied skeptically. “Well anyway have a napkin ready. I’m sure he doesn’t want to blow in his pants that’s gross.”

Rory grimaced. “That’s crude.”

“It’s the facts!” Ama defended. “You’re already having sex with him, these are the cold hard facts of what you’re doing with him girl. Get used to it.”

Rory sighed. “Fine. Thanks for the advice.”

“I’m pretty sure he’ll like whatever you do to him Rory so don’t worry about it.”

“I hope you’re right, he’s been with a lot of girls that I’m sure were much better at this.”

“But he’s with you. Act like it,” Ama encouraged.

Rory raised her eyebrow at that advice. She gave Ama a short nod and finished her gelato before it melted.

****  
That night, Rory and Jess sat in the back of the mostly empty movie theater. There weren’t a lot of movies that caught their eye so they decided to just see Troy. Jess figured it would have some good action scenes and Rory could really watch and mock anything. It’d been out for awhile now so not many more people needed to see it. There were a handful of people that filled the stadium theater seating and the couple took advantage putting their feet up and taking out the snacks they’d bought at Wawa before going to the theater.

“The red vines were a good choice Gilmore,” Jess praised.

“My mother taught me well, a movie is a no good without the appropriate snacks,” Rory whispered in between handfuls of popcorn. The two sat and watched the movie, giggling every time they thought Brad Pitt was particularly ridiculous in his role. They held hands and got as close as they could, Jess wrapping his arm around Rory’s shoulder. 

It wasn’t until the sex scene Brad was in that the air changed between them. Rory’s senses came heightened and the comforting and innocent way Jess’s thumb stroked her bare shoulder felt like a come hither motion. Her breath became more shallow and she snuck a glance towards Jess who was watching the movie intently and didn’t seem to notice Rory’s arousal. What was it with her needing him when they were in public spaces?

“Jess,” she whispered. Jess hummed and shifted his eyes towards her. She bit her lip and tilted his head towards her so that she could kiss him softly. It was close mouthed for a minute, Jess tentatively kissing her to see where her mood was. Rory probed his mouth for more, deepening the kiss. When he wouldn’t oblige she became frustrated and bit his lip lightly. That alerted him and he surrendered, opening his mouth to her and letting her explore. They made out like teenagers, ignoring the movie completely at this point. They didn’t like it anyway.

Rory felt confident to take things a step further and took her hand from Jess’s face to trace it down his chest. She reached his jean covered groin and just as she suspected, she could feel him rock hard. She carefully used her hand to rub him, tease him as she continued to kiss him. Jess quietly moaned and brought her as close as he could with his arm still wrapped around her shoulders. He broke the kiss and whispered against her lips. 

“Hope you’re not teasing me Rory, especially here.”

“I’m not,” she confirmed with a glint in her eye. 

Jess raised his eyebrow in disbelief. “You’re wearing jeans and we’re in a movie theater, I know we’ve done public sex but this is a stretch.”

Rory shook her head. “Don’t have to have sex,” she breathed before taking his lips again. She unbuttoned his jeans and slowly lowered the zipper to not alert the patrons a few rows in front of them of what was happening. A big action scene was occurring thankfully so it drowned out any noise and no one else was around them. Rory reached into Jess’s boxers and felt the silky skin of his dick. She pushed his pants down a little to create some relief and room for her to take him out. Jess broke their kiss again.

“Rory you don’t have to do this,” Jess whispered harshly. Rory shushed him.

“You do so much for me and I want to. Just do one thing for me.”

“What?”

“Tell me what you want,” she instructed him nervously. It was nothing like when he said it during sex. He could tell that for all her boldness, this was new territory for her. He smiled and kissed her, signaling his agreement.

Rory put her hands around him, fisting him from the base. She looked down and saw his pre-cum surrounding the tip and twisted her hand up to reach it. She used it to create a better glide as she stroked up and down twisting her hand slowly. Jess’s breath was ragged and his eyes closed, holding back to not to groan out load. 

“Is it good?” she asked against his ear.

“Faster,” he grunted.

She acquiesced moving her hand up and down faster, changing the motion of her hands with every rotation. 

“Yes,” he hissed. “Just…focus on the tip baby, rub your thumb on the opening.” She obliged him and found his body was shook when she did that. She kissed his neck and licked his earlobe, remembering that he also liked it when she played with that part of his body. They continued on for a few minutes, Rory changing her tactics and even exploring down to his balls. She brought her lips back to Jess’s once she sensed he was getting close. 

“God I’m so close go faster baby. You’re amazing,” he praised. She increased her movements and flicked her wrist frantically. She watched as Jess gasped against her mouth. She’d never seen him so powerless to pleasure between them before. She looked around remembering suddenly Ama’s advice about a napkin and used her other hand to reach for the bunch they put in the cup holder between them. She crashed her lips against Jess’s to muffle the last groan and moan he let out as he came, Rory catching his release with the napkins. She continued to kiss him as he came down, peaking an eye out to see if anyone noticed them and saw they were still in the clear since the movie was reaching its climax. Rory released both his lips and his cock, putting him back in his boxers and fixing his jeans. She wiped her hands with more napkins and put them in the Wawa plastic bag so they could be thrown away. Jess watched her in disbelief all the while.

“Was that good?” she asked hopefully once she was done.

Jess nodded. “Let’s go back to the apartment.”

Rory giggled and agreed, gathering up their things. At the sound of their rustling and giggling the other patrons finally turned their heads towards them in annoyance since the movie was starting to quiet down in its action. The couple laughed even harder as they scurried outside the theater into the humid summer night.


	11. Chapter 11

**Notes for the Chapter:**

> A short chapter tonight, but I feel like this stands on its own within the story that other scenes after it would be pointless. I intended for other plot developments but they took me to a different place, because it's Jess and Rory. Hope you enjoy!

It was the next morning and another sunny day in Philadelphia finding Rory and Jess cuddled against each other under the covers. Jess hadn’t been able to keep his hands off of Rory in some way shape or form since they’d left the movie theater last night. He was curled around her back, hand under her tank top stroking her stomach. His head was leaned over her shoulder reading her book with her. She had been reading a book of Pablo Neruda poems and was trying to convince him slowly to gain an affinity for poetry. He didn’t quite get it, but she seemed to love it and he liked the pensive look on her face when she read it. Every poet she made him read gave a particular kind of expression. When they read Emily Dickinson her pensive look was more frustrated than anything, trying to decipher the riddles between the lines. He couldn’t deny that Pablo was sexy though.

“Read this one,” he heard her instruct him. She turned her head towards him and gave him a soft look that worked to convince him to do many things. “Please?”

He grunted in mock annoyance and leaned over a little more to get a better look at the page. He started to read, his voice still full of sleep, hoarse and gruffer than usual. He leaned down, eyes still on the page to speak into her ear, feeling her shudder at his words.

Barely  
risen from sleep,  
I relinquish the water,  
enter your sleeves,  
my legs look for  
the hollows of your legs,

He stroked her stomach, kneading her skin around to her waist, to the underside of her breasts. Once he finished he laid a simple kiss on her cheek and she murmured a thank you while she closed the book. She turned on her back to look at him, stroking his face and rubbing her thumb against the bristles of his five o clock shadow that was forming. She liked it, wanting him to keep it since he always seemed to groom it or shave it completely. There was a childish pride to it all, the fact that she had this man with her. Rory Gilmore, the bookish academic girl who never really seemed to care about boys or fitting in with the rest of the crowd was able to find this perfect nook with a man who wanted to understand her, could match her wit and love for music and books, and showed her new places. It felt perfect. 

“I think I actually like that one,” Jess admitted. Rory grinned and patted his cheek playfully. “I knew you would!”

“I will give Neruda this, his words are sexy. Very soulful. Every time we read this together you know I just want to be inside you, do what he’s saying. Look for the hollow of your legs, snap your threads.”

“Didn’t you do that enough last night?”

“Can’t help it,” he shrugs. “It doesn’t bother you at all does it?”

Rory furrowed her eyebrows. “No, no it doesn’t. I…I like what we do?”

“You do?” he smirks. “What do you like about it?”

“Jess,” she groans, turning beet red. 

“I can tell because you’re responsive as hell but I wanna know Rory. I realized after last night with how nervous you were to touch me that I don’t always check in with you about our sex. You get nervous about how experienced you are compared to me and I should remember that.”

Rory’s gaze softened. “That’s really sweet.”

“So tell me, what do I do to you that you like?”

He kept his gaze on her, not letting her get away with not answering. He smiled encouragingly and kissed her cheek. “It’s ok, you can tell me.”

She sighed. “You really wanna know?”

“I do!”

“Well…I like your hands, when they put pressure on my skin.”

“Like this?” he asks pressing his fingers against the underside of her breast. Her breath hitches and he smirks.

“Yeah like that. And when you hold my neck and press against my nape, clench my butt when I’m on top of you, and hold my breasts from behind,” she rambled unable to stop telling him everything on her mind.

Jess’s mind was bright with the images she brought up and his body stiffened around hers. He leaned down to kiss her neck feverishly and held her breast tightly making her moan in surprise. 

“Keep going, tell me more,” he said hoarsely. 

“I…oh god,” she felt him taking off her panties and reaching between her legs, feeling the wetness and rubbing her clit. “I like when you go down on me, I like when you’re top of me and have your fingers in me and you look at me and smile. Oh god Jess please.”

“Hand me that condom, open it.”

She scrambles to reach his nightstand, picking up the plastic square and opening it quickly. She hands it back to him and rolls it on carefully before lifting Rory’s leg and entering her swiftly and easily. They groan at the same time and Jess starts a steady pace, leaving just the tip before thrusting hard leaving her breathless every time.

“Tell me more Rory,” he grunts.

“I like when you talk to me, when you tell me how good I feel, how much you like it. It makes me feel…oh…it makes me feel beautiful.”

She turned her head towards Jess and looked in his eyes, leaning her forehead against his. They panted as he continued to thrust in her. Rory held Jess’s face, kissing him softly, taking his lower lip and biting it. He growled and she grinned, loving the reactions she evoked in him. He held her leg higher and shifted them so that Rory was half on her stomach, allowing Jess to thrust deeper.

“You like this?” he grunts. He pushes her leg to the bed and presses his fingers against the inside of her thigh and she cries out. 

“Yes!” 

He leans down again to press his back against her body and uses his other hand to brush her hair back from her face. He kisses her neck softly in contrast to the rough way he continues to fuck her. 

“Jess please, please talk to me,” she pleads. She needs a little more, he’s giving her so much but she just needs that little bit to put her over the edge.

“You want me to tell you how good you feel?”

“Please,” she cries.

“Fuck you know how good you feel, I can’t stop Rory I want you all the time. I want you when you’re reading a book in the store, I want you when you’re lying on the grass in the park and hiding from the sun, laughing at a movie. I want to make you feel good all the time.”

She was breathless at this point, unable to do anything but hold onto the sheets and wrap her arm around Jess’s neck tighter to ground herself. She buried her head in the pillow feeling overwhelmed, crying out. Jess laid his head next to hers and kissed her ear repeatedly, continuing to whisper to her.

“You’re amazing Rory. Fuck, I don’t know what you’re doing to me I want you all the time.”

“God, Jess please. Please.”

He reached around her hips and furiously rubbed her clit, immediately causing a vice grip around his dick. She cried out repeatedly as she came, closing her eyes tightly and gripping Jess’s neck, digging her nails into his skin. He slowed down his thrusts as she came down, kissing her cheek and shushing her as she sought for control over her breathing. She knew he was still hard once her senses came back to her and that he hadn’t finished yet. She released her arm from around him and pushed him off her so that she could get on her back. She plopped back down on the bed and reached for him with tired eyes mumbling C’mere. 

He gently got on top of her, between her legs that welcomed him back in her. He sighed and leaned his forehead against hers again and kissed her softly as he thrust in her at a steady pace. She stroked his hair and his back, opening her mouth to him to deepen the kiss. She tightened her legs around his waist and moved her hips in tandem with his, hissing as he started to hit the right spots in her body again. They broke their kiss and Rory looked into his concentrated face, seeing he was almost there, but he needed something, he needed something more. He always gave her so much and she needed to know how to get him there, how to leave him powerless to her like she did last night.

“What do you need?” she breathed against his lips. She kissed him quickly and gripped his hair. 

“I don’t…I don’t…” he struggled to form words, still concentrating on the right rhythm to get him to the tipping point. She trailed kisses from his cheek back to his mouth.

“You make me feel so good Jess,” she told him when she broke her kiss. “No ones ever made me feel as good as you, made me feel so wanted. It’s scary, it’s so perfect, you feel so good every time.”

“Oh god, Rory,” Jess buries his head in her neck again, losing his rhythm. “Keep going, please.”

“Please come Jess, please. Like you did last night in the theater, let me make you feel as good as you make me feel all the time,” she whispers in his ear. He cries out and convulses against, coming hard. Rory sighs and closes her eyes in satisfaction, leaning head back, continuing to stroke Jess’s hair as he comes down. All you can hear in the room is the sound of the breathing coming back to a steady pace. 

After a few minutes Jess raises his head and kisses the hollow of Rory’s neck softly, trailing kisses until he reaches her lips, giving her a fiercely hard kiss. 

“Holy shit,” he laughs. “Rory what the fuck?”

She laughs along with him. “That was…”

“That was intense.”

“That was more than intense. I didn’t know Pablo made you that hot.”

“It’s not Neruda, you know it’s all you.”

“Jess…”

“Look I know what I said yesterday about not doing relationships but…it’s never been that intense Rory. I can’t see myself letting go of you when you leave here.”

She smiled shyly, wanting to hide away from his intense gaze despite the incredibly intimate things they had just been doing. This is what he liked about Rory, how she didn’t understand how beautiful, smart and funny she was. Enough that she had caught his attention, kept it, and expanded it continuously.

“So what does that mean?”

“It means, that when you go back to Stars Hollow and Yale, and some guy sees the same things I do and wants you as much as I do, I want you to remember that there’s a guy in Philadelphia that doesn’t want you to leave him.”

Rory’s eyes widened. “Does that mean you’re my boyfriend?”

Jess grimaced. “I haven’t been a boyfriend in years I don’t even know what that means anymore.”

Rory giggled. “I can teach you…tutor you even. You’re a very fast learner after all.”

“Can we take it slow on the calling me your boyfriend part? It’s just more than I’m used to,” he admits.

She bites her lip. “I guess. I can give you that.”

He kisses her again softly. “I’m gonna tell Chris and Matt I’m not coming in today. Let’s go to Ultimo, that’s next on your coffee shop list.”

Rory’s face brightened. “Really! I told Matt I would come in today though.”

“I’ll tell him we’re both taking the day off, you’re doing the First Friday stuff tonight anyway. We’ll stop by Truncheon before we go, get whatever you need and the leftover zines he wants you to give out. Sound good?”

She nodded and kissed him again. “Yeah it sounds good. It all sounds really good,” she said against his mouth.


	12. Chapter 12

Days later, Jess doesn’t regret basically agreeing to be Rory’s…boyfriend…but he sure regrets even mentioning it to Matt and Chris.

They interrogated him one day when the three of them were getting lunch on Monday. Rory was doing some work on her article for the zine and waved the three of them off saying they needed guys time and she needed to actually concentrate. Once they settled down they teased him mercilessly, noting that something had changed between the two of them over the weekend. 

“Isn’t this around the time you start getting bored and find reasons to nitpick the girl you’re dating?” Chris asked. “I’m surprised Rory has lasted this long.”

“Yeah don’t fuck this one up, she’s actually lightening up my load on the zine,” Matt added. 

Jess rolled his eyes. “Who says I get bored after like a month?”

“We do,” his friends replied simultaneously. 

“It’s all fun and games but then it comes time for some actual commitment and you can’t hack,” Chris explained. “So is this the same thing once Rory leaves and goes back to school?”

Jess gritted his teeth in annoyance, mostly because they were right and that was his MO. “No.”

“No?” Matt questioned. “As in no this isn’t the same thing?”

“Why isn’t it the same thing?” Chris added.

“Because…I basically told her I didn’t want it to be over once she leaves,” Jess groans.

The boys eyes widen and they let out a happy woop, shaking Jess’s shoulders. 

“Is she your girlfriend?” Matt teases.

“Can we not guys? Let’s just eat. All I know is she’s great, I’m great, it’s great being together and I’m glad it’s a thing. Can that just be it for now?” he tells them firmly.

The boys sheepishly nod and start to eat their sandwiches. They eat in silence for a few minutes before Chris quietly breaks the hush over them.

“She’s definitely your girlfriend.”

***  
Ama is just as bad.

Jess finds it hard to meet new people, so when Rory introduced him to Ama during First Friday and left them to their own devices while she went and interviewed the artist she needed to for Matt, he was worried his introverted tendencies would fuck him over and make this new important friend of Rory’s think he was a creep. Thankfully Ama seemed to get his dislike for small talk and noted how dumb it was as well. 

“We don’t need to do the small talk thing, I don’t really need to know where you’re from and your sad family history because I can tell doing all that will make you bolt so how about we sit in that corner and pick out the worst piece of art and see if there’s any guys around here worth it for me to take home tonight?”

He simply nodded with a smile and followed her to an empty bench, both holding a glass of cheap wine they proclaimed was unnecessary if it was going to be so tart and managed to single out a bearded red head man that Ama deemed good enough for the task of ending her sex drought. He was surprised to see at some point during the night the way her eyes glazed over when she stared at a short brunette with long blonde hair, a curvy body and a nose ring. It was the kind of girl he probably would have went for if he didn’t have Rory with him. When he and Rory walked over to the gallery and she talked up Ama and joked about her quest to end her horniness, she’d only mentioned Ama’s specific types for a man. She’d never said anything about women.

He didn’t say anything but merely observed from the corner of his eye the way Ama’s eyes followed the girl for a minute, biting her lip. But then the red head man she ended the night with walked in and diverted her attention for the rest of their time. He played wing man for her and actually kind of enjoyed it. She was everything Rory said she was-blunt but with a politeness so that you could never say she was being a bitch. She seemed to like Rory, noting that they hadn’t been friends long but that the girl had an innocence and wit that seemed mismatched but fun to figure out.

He and Rory had lunch with her on Thursday, getting a quick break from the craziness at Truncheon. He’d suggested a meal at Monk’s since he was strangely craving mussels and Ama exclaimed to Rory that she’d found a good man with good taste. The three sat and Jess listened in and out of a conversation the girls had about Ama’s 2nd date with Jerry the guy she met on Friday.

“He told me I’m the first black girl he’s slept with and thought it was some prize of a compliment, I wanted to smack him,” she told them rolling her eyes. 

Rory’s eyebrows furrowed in confused thought. “Why would he tell you that?”

“He probably thought it would make me feel special, that he grew up in the white suburbs, came to the city and is now open to the world of dating black women. I mean that’s cool but I don’t need to know all that.”

“So what’d you say to him?” Jess asked with a smirk, already guessing she let him have it.

“I told him if he kept thinking he’d get a prize for it I’ll probably be the last black girl he ends up dating.” Ama tells them with the wave of a hand. “He’s dismissed I don’t have time for that.”

Jess laughed while Rory frowned, obviously bothered by the interaction. Jess looks and sees her expression. “What’s up Rory?”

“It just sucks he made you feel that way, he should just like you for you,” she says sadly. 

Both Jess and Ama smile softly at Rory, already experienced with the ways Ama’s features set her apart in the minds of some people. Jess saw it all the time growing up in New York in Latino and black neighborhoods. Rory lived in a bubble for all her life and that was hard to remember sometimes. She still seemed to have this innate belief in goodness. 

“It’s ok Rory. I mean it’s annoying but it’s ok. He should just like me for me and not think of me or himself as a special snowflake given the circumstances but there’s more where that came from,” Ama explains indifferently. “Plus he was a pretty selfish lover, I don’t know why I even went on that second date. Free food?”

Jess laughed and Rory was able to muster up a smile, eating her fries daintily. The three continued on with their meal until Rory’s phone rang. She reached in pocket and her eyes widened at the name on her caller ID. 

“It’s my mom,” Rory mumbled. She continued to stare at the phone, not knowing whether to answer it or not. 

“You should take it, she’s actually calling you for once,” Jess whispers. Rory nods and excuses herself from the table, hurrying outside to take the call. He and Ama watch her go, similarly hoping this call did not end in frustration and tears. 

“Her mom usually doesn’t call her, Rory has to make contact these days,” Jess notes. “She calls her like once a week maybe? But the conversations never last more than five minutes because they’re full of the general check up niceties. She cried the first time.”

Ama gives him a sad smile and takes a sip of her beer. “She told me a little bit about it, it sucks.”

“It does. They’re close.”

“I told her it’s not surprising. That in the end her mom is her mom and no matter how cool she is she thinks her daughter’s life should be a certain way. And I guess shacking up with a 23 year old guy in a strange city isn’t part of that.”

“I wouldn’t think so,” Jess agrees.

“Good,” Ama says putting her beer down. “So I hope what’s happening here is worth all of that grief,” she tells him with a serious face.

Jess pauses, scrutinizing Ama for a moment. He didn’t think her blunt nature would be turned onto him. “Excuse me?”

“I like you Jess, you’re very much living up to the hype of Rory’s words. She seems very happy with you. But I hope you remember this isn’t her real life, here in Philadelphia. That she has a whole world that includes a mother she considers to be her best friend. And she should make whatever choices she wants to make, I really believe that, but I hope that whenever she leaves here, whether it’s tomorrow or the day she has to go back to Yale that she doesn’t leave here thinking you wasted her time.”

Jess swallowed hard, shrinking under the hard gaze of this girl. “Did she tell you about Friday morning?”

Ama shook her head in denial.

“I told her that I couldn’t see this ending when she leaves. Look I have a hard time with relationships, it’s probably because my mom fucked me up with her flakiness and bad string of boyfriends when I grew up. I had one girlfriend in high school but she was more like my best friend I would sometimes fuck. I don’t know what a good relationship looks like.”

“Well I hope you can figure that out because Rory doesn’t seem like a fling kind of girl to me. She seems like a relationship girl. I haven’t known her very long at all, but she is so determined to be as good for you as she thinks you are for her. That’s not a girl that let’s things go after a couple months,” Ama observes.

“You’re right. You are. And I knew that going in but I still did it. I still told her to come here, I didn’t tell her to leave when she did, and now here I am wanting to try to be what she needs.”

Ama nods. “Good. Well your trying may have to start again soon if that conversation outside doesn’t go well. Step one in being a supportive boyfriend.”

Jess grimaces. “Don’t say boyfriend.”

“Boyfriend,” Ama challenges. “It’s what you’re working towards. Say it with me…boyfriend.”

He frowns and eats some fries in protest. Ama chuckles and takes a long draw of her beer. “She’ll get you there,” she promises.

After what seems like forever Rory walks through the front door with a sheen of sweat on her face from the humid, hot weather. She has a worried look and once she locks eyes with Jess she bites her lip in nervousness and returns to the table slowly. 

“I have to bail on our trip to the arboretum on Saturday Ama, I’m sorry,” Rory says sadly. 

“Oh…it’s ok. We’ve got time I guess. Why what’s up?”

“I…I need to go home. I need to go back to Stars Hollow.”  
****  
When Rory gets outside and answers the phone she’s not sure what to expect from her mom. Their short phone calls during her time in Philadelphia had been painful, not because her mother was harsh or mean with her words but because of how short and plain they were. Rory would call, wanting to bridge the gap and find some way to make Lorelai understand where she was coming from, but all she got was a brick wall. They would exchange hellos, Lorelai would ask if she was ok, if she had enough money, and if she was coming home yet. Rory would reply, yes, yes, and no she wasn’t coming home yet. She wasn’t ready. Lorelai would stew in silence, Rory would ask after Lane and meekly ask how things with Luke were going. That always felt touchy, a subject that would bring rapturous stories if things were normal between them but all Rory got was a simple good.

Rory cried after the first time but she refused to the next. Jess looked almost guilty when she cried, knowing that he was a catalyst to all of this but in the end these had been Rory’s choices and he had in no hand in them. He didn’t make her do anything and he certainly didn’t make her mother take a turn and become more like Emily in the way of holding her daughter to an unachievable expectation of morality.

Lorelai hadn’t called her before though, so maybe this was a turn.

“Mom?” she answered earnestly. She waited a beat for a voice to take over.

“Hey kid,” her mom answered. Her voice was scratchy and Rory recognized right away it was the way her voice turned when she’d been crying.

“I…were you crying mom?” she asks concerned. “What’s wrong? Is everything ok? Are grandma and grandpa ok?”

“Everyone is fine,” Lorelai assures her. “Mom is still away and dad is living like a bachelor. So weird.”

Rory laughs at the thought. “I can’t imagine that, I bet he’s still afraid to go in the main house thinking grandma will catch him all the way from Europe.”

“Oh you know it,” Lorelai agrees. “The Gestapo have eyes everywhere!”

“Mom!” Rory chastises. This felt all too familiar.

“Sorry, sorry no more Hitler jokes.” Lorelai promised.

Rory giggled and a silence passed between them.

“How are you Rory? Are you safe? Do you need money?” Here it was.

“I’m good…I’m really good mom. I’m safe. I don’t need money,” she answers mechanically.

“Good…good.”

“How is the inn?”

“Good.”

“How is Lane?”

“Good.”

Rory grows frustrated at this point, sick of having this same conversation over and over when she knows what’s going to be said. “Mom why did you call?”

“Excuse me?”

“We do this every time, you don’t want to actually talk to me until you hear me say I’m coming home. But I’m not coming home right now, I’m not ready.”

Her mom lets out a big sigh. “And why aren’t you coming home huh? Jess hasn’t gotten sick of you? What are you going to do if this fling you’re having blows up in your face tomorrow? What are you doing Rory?”

“I’m with him mom! I don’t understand why I have to keep explaining this to you?”

“You didn’t even know anything about him Rory except that he wrote a book when you ran away to him Rory.”

Rory clenched her eyes and let out a hard breath. “That’s not fair. I know a lot about him now.”

“Oh really,” Lorelai mocks. It’s almost like a challenge. 

“Yeah, I do. I know that his birthday is Christmas Eve and that his mother was so hopped up on drugs that she intended to name him Jesus but forgot the U. I know that he didn’t graduate high school because he thought it was more important to find his father who abandoned him as a baby so that he could finally figure his life out. I know that he likes vanilla coffee, he doesn’t burn in the sun easily, and when he drinks whiskey he’s more likely to reference Notorious B.I.G. lyrics. He writes best when he’s by the water even though he hated California so he rented a shore house for us in a couple weeks so that he could finally break his writer’s block. And most of all I know that when I do leave here this will not be a fling because he told me it wouldn’t be. That I shouldn’t be with anyone else because he doesn’t want me to leave.”

She was breathless and holding back tears, so angry that she had to defend herself and defend Jess against someone she always believed was so…cool. It was surprising to her that for all her mother’s missteps, she’d forgotten them so quickly and turned it around to judge Rory harshly.

“He wants to be with you?” Lorelai asks weakly.

“He does,” Rory confirms.

Silence takes over again. 

“You’re going to burn like hell on the beach,” Lorelai finally says.

Rory rolls her eyes. “Seriously?”

“It’s true!”

Rory smiles to herself, leaning against the building for support and looking out into the crowd of people walking up and down the street. 

“I just miss you kid. You’ve been so off lately, especially before you left. You have to understand that what I was seeing, it wasn’t the kid I raised. I didn’t raise you to be that irresponsible, I didn’t raise you to be…the other woman in someone else’s marriage. You know Dean is still with Lindsay?”

“I don’t want to talk about Dean mom,” Rory hisses.

“Well we have to at some point. You had sex with a guy you don’t know, kissed your married ex-boyfriend, and then ran away to live with your one night stand you knew nothing about for the summer. It’s just not what I wanted for you.”

“And you’re entitled to that because you’re my mom, but you’re also supposed to be my best friend. Isn’t that what you tell me all the time?”

“Well I pulled the mom card.”

“You can’t do that! You can’t just play that card when it becomes convenient!”

“That’s not what I’m doing!”

“Yes you are,” Rory says firmly. “You’re playing your mom card to judge me right now when a best friend wouldn’t do that. Mom I’m an adult now and I have to make my own decisions. When I was younger you could do this and I had to go with it because you had the pop tarts and the money for the coffee but it’s not like that anymore. You can’t do this.”

Her words get caught in her throat by the end and she feels a cry coming on. She swallows hard and tries to continue.

“It really hurt when you tried to dismiss me to Europe like I was some shameful person you had to hide away. It was so…it was really Emily of you. And I didn’t expect that. I probably would have gone with grandma on my own with my own convincing but once you did that I couldn’t do it. So I came here. And I’ve been really happy here mom. Jess is so great, and you’d like him actually. I made this great new friend and I swear you’d want to shop in her closet. I’m working with one of the guys at Jess’s publishing house and interning with him on the zine they do. I went to this art gallery Friday night to interview an artist and it was so weird but it was fun to write about because it was different. I eat Philly cheesesteaks all the time even though Jess hates going and I’m working through a list of all the coffee shops to declare which place is the best by the end of the summer.”

Lorelai continued to not say anything but Rory could hear her crying and her heart sank. She hated that.

“For what it’s worth I miss you too. I miss you so much,” she whispered.

Lorelai continued to cry, “I was like Emily? God, Rory how could you…I was like Emily?”

Rory rolled her eyes. “That’s all you got about that?”

“What kind of mother am I?” Lorelai cries.

“The kind that had a daughter who didn’t rebel for 19 years?” Rory questioned.

Lorelai laughed through her tears. “You really know how to work through a phase kid I’ll give you that.”

“I am a perfectionist. Can’t stop until it’s right.”

Her mom sniffled. “I’m really sorry you felt that way kid. I just wanted to protect you.”

“I know you did mom…I know.”  
***  
The short walk back to Truncheon is quiet. Rory walks behind Jess with her head down, unable to look at his body fraught with tension and stalking down the street. She walks fast to keep up with him but she’s just barely able to do it. She realizes now that she didn’t explain herself or her impending departure very well. And she probably shouldn’t have just done it with Ama as an audience. Both of them had looked at her surprised, but once the words settled in, Jess’s jaw clenched and he mumbled that he had to go to the bathroom and that they should be getting back. He dropped some money on the table and basically did god knows what in the bathroom until they were ready to go. Rory informed Ama more about what was causing her to leave and they said their goodbyes with the possibility to have a quick coffee and chat before she left the next afternoon.

She paid for their lunch and once Jess came out of the bathroom he led them out without a word.

When they arrived back to Truncheon he picked up his notebook and told Matt and Chris he was taking the rest of the day off to write by the river. It had been working for him lately but not enough to totally push through some of the blocks he was experiencing with his writing.

He ignored Rory as he walked out the door and she blinked back tears, not used to this cold, angry side of Jess. She imagined that when he got mad it would be visceral and harsh but not this. Rory looked to Matt and Chris and told them she would be back in a few minutes. She knew she had to finish the layout of the zine for the printers tomorrow but this was important.

She ran outside and saw Jess already down the street, still walking fast. She had no choice but to run after him, glad she wore her keds today instead of the cute sandals. It never seemed like she was getting near enough to him so she shouted out to make him possibly slow down.

“Jess, wait!” she yelled.

He stopped but didn’t turn around, walking to the side to move out of the way for passersby going at his pace. He turned towards her, arms crossed and waited until she came to a slow stop from her jog, panting and holding her hip.

“I didn’t know you could walk that fast,” she said breathlessly. He didn’t respond, looking past her. They stood for a few minutes while Rory caught her breath.

“Shouldn’t you be packing?” Jess finally mumbled. “It’s not like you brought much but I’m sure you’ll want to hightail it out of here soon.”

“Jess, no it’s not what you think! I’m not going back, going back. I just need to go for a few days, a week at the most.”

“Oh,” his hard exterior softened at the revelation. 

“Yeah. I should have phrased it better earlier.”

“Well I jumped to a conclusion.”

“You did.”

The two fell back into silence and Rory wiped the sheen of sweat on her face. 

“When are you leaving?” he asked.

“Tomorrow afternoon. My mom wants me to come to Friday night dinner with my grandpa.”

“So you two are ok?”

“We’re getting there, that’s why I’m going home. We hashed out a lot of things over the phone earlier but it’s not the same. I think if I wait this out totally all summer it’ll make things worse once I go back. And even though I was so mad and hurt by her, enough to run away, she’s still my mom. She’s really important to me. So I have to go back just to make sure things will be ok for her and me because I would hate for it not to be. Can you understand that?”

At a certain point, he couldn’t because this was not at all the relationship he shared with Liz. But he could understand that Rory didn’t feel whole right now and that was largely because she didn’t have her mother to share in any of her joys with. She had told him this quietly in bed yesterday morning when he’d asked her how much she missed her mom. She broke down and he held her as she talked about how happy she was here but how lonely it was for her best friend to not see that. 

So he didn’t understand it for himself, but he understood Rory needed this.

“I do,” he tells her, taking a step towards her. She takes a step towards him and reaches for his hand. 

“I promise I’m coming back. I’ll even leave something you know I can’t live without for more than a week so that you see,” she promises.

“You don’t have to do that Rory. If you say you’re coming, I have to trust you’re telling the truth. And that’s what this whole relationship thing is about right?” 

“Yeah…yeah it is. And I will call you because I’ll miss you.”

“Yeah I was getting used to you kicking me at night,” he smirks.

She scoffs and shakes her head. “I do not do that!”

“Yes you do and I get a glorious week break from it,” he mocks.

“Whatever, you know what else you’re getting a break from,” she challenges.

He thinks that over for a second and frowns. “Whatever I’ll just call you.”

“Ew, I’m not doing that!” Rory throws her hand up in disgust.

“Don’t knock it till you try it.”

“I’m not having phone sex with you in my childhood bedroom,” she opposes.

“Whatever you say, you’ll have a drought too.”

He’s smiling now, his face brighter than when he left Truncheon and Rory feels relieved. 

“Were you that hurt Jess…that I was leaving?”

Jess blushes and looks down. “I mean…we just kind of figured out what was happening with us and then you just leave…”

She pulls him closer and leans up to kiss his cheek. “I swear I’m coming back. You’re going to go to the river and do some writing, I’m going to finish putting together the zine and when we’re both done I want a banh mi sandwich for dinner and you get to pick a movie.”

He fights the grin on his face. “Even if I pick Almost Famous even though you keep saying you hate Kate Hudson?”

She resists the urge to protest and takes a deep breath. “Even if you pick Almost Famous.”

He nods and kisses her cheek and then her lips quickly. He reluctantly lets go of her hand and waves as he walks off into the crowd. Rory watches him go until she couldn’t see him anymore before turning around and slowly making her way back to Truncheon. 

This was the right thing to do, she thought to herself. The best way to restore some kind of order to all the parts of her life. 

She was happy with Jess, but what would that mean if she and her mom weren’t ok?


	13. Chapter 13

Stars Hollow was quiet.

She always knew that about her town but there’s something startling about it now. Even when she is out walking about the town while she waits for her mom to get home from the inn, the hustle and bustle doesn’t sound the same. It’s muted and like a soft echo when compared to the outside of Jess’s apartment, reggaeton music playing and neighbors fighting with each other. 

She greets everyone with a fake smile as they exclaim that she’s returned. She kindly informs them that she’s only visiting. When they ask where she is she tells them Philadelphia on an internship. They don’t need to know the details of her life with Jess. 

She passes by Doose’s on her way to Luke’s, because Lorelai texted her to say they should just meet there for a pre-dinner dinner. She sees Dean through the window, checking out a load of groceries for an older lady. He has a sweet smile on his face that she remembers from throughout their time together and she smiles nostalgically to herself. Dean would always be her first love, but it was a feeling that passed over time. She spent her entire freshman year at Yale still unwilling to really truly move on from that feeling until Jess came along and showed her something different. 

She moves on before he can see her. She doesn’t want to have another awkward conversation with him, see if he’s finally moved on as well to either make his marriage with Lindsay work or back out of it so that he can move on as well. 

She walks into Luke’s and the chime of the bell turns everyone’s attention towards her. She gives everyone a warm smile and a wave, breathing in the scent of Luke’s coffee and lets the feeling of home wash over her. She loved the coffee shops in Philadelphia and fun things she discovered at places like La Colombe and Ultimo, but nothing could really beat Luke’s in the end. Greetings from various townspeople were directed towards her as she made her way to the counter where Luke stood, looking at her warily but with a smile. 

“Hey Luke,” she greeted. He gave her a small smile and proceeded to put a big mug in front of her and poured her a cup of coffee. 

“Glad to see you back Rory,” he greeted back as he topped off her mug. 

“I didn’t even have to ask!” she exclaimed surprise. 

“Yeah well I hear you’ve been scoping out and loving some other places in Philly, had to remind you what real coffee tastes like.”

She takes a sip and quietly moans as the rich taste. “Don’t worry I don’t forget so easily where I come from.”

He continues to work quietly, taking orders and making a new pot. Rory drinks her coffee silently and watches him. He seems lighter somehow and she wonders if that has anything to do with him and mom being a thing.

“So things have been good Luke?” she questions.

“Eh same old same old around here. Taylor is deciding whether he wants to do the Lazy Hazy nonsense at the end of the summer again. Trying to rope me into hosting a barbeque for it this time but I won’t agree until the last minute just to annoy him.”

She giggles. “Sounds like some things don’t change.” She hesitates before asking her next question. “And things with my mom? They’re…good?”

A rare smile that Rory has seen a handful of times in her life appears on his face. “Yeah things are good, Rory. What about you two?”

“They’re getting there, that’s why I’m here this week.”

“Well good. She really missed you while you were gone kid.”

“I missed her too,” she said sadly. 

“But you’re happy…out there in Philadelphia? It’s good?” he asked her hopefully.

She answers with her own bright beam. “Yeah it is. Jess is really great, you don’t have to worry about that.”

His eyes avert from hers, feeling awkward talking about her relationship with his nephew. He clears his throat. “Well that’s good. I’m glad.”

She giggles and continues drinking her coffee. A few minutes later the bell of the door chimes and she turns to see her mother walk in the door. It’s the first she’s seen her since she got back this afternoon. She gets up immediately and jumps into her mother’s arms. They both say nothing, grinning and giggling as they hold each other for a few minutes ignoring the strange looks they receive from the other patrons. 

“Fruit of my loins!” Lorelai exclaims. “You’re here!”

Rory laughs and breathes in her mother’s perfume that she’s worn her whole life. This coupled with the smell of coffee calms her spirit. By the feeling of home she feels in her mother’s arms in her favorite diner she knows everything here will be fine.  
***  
It’s not until that night that Lorelai and Rory are able to really sit down and talk. Dinner with Grandpa had been fun. They had drinks and a dinner full of appetizers, which was just the kind of atmosphere the three of them needed. Grandpa asked her all about her time in Philadelphia, still under the guise that she was there on an internship. She and Lorelai worked to create a pretty elaborate plot. It did involve Jess, Rory just told him that she met Jess at the wedding and talked about Truncheon and the work they’d done and he offered her an internship there. She was staying in the apartment above the store for convenience sake. Rory didn’t necessarily have to lie about much, except that she was shacking up and having sex with an older guy all over the city.

The women settled into the couch that night, sharing a bag of gummy bears as Rory told Lorelai about the first time she met Ama. Lorelai laughed and listened interested in this world Rory had created for herself. She was relieved to at least see that not everything was about Jess in Rory’s life in Philadelphia. She’d made a friend and she had a job, albeit one that didn’t pay, but she seemed to have a life there.

“You’d really like Ama, she dresses in these amazing vibrant colors all of the time that I would never be able to pull off. Lots of yellows and oranges. And coral! And her parents are from Ghana so she has all these clothes made for her with really cool prints from there. I don’t know she’s just really different from most people I know, really honest. And grew up differently than I did but really likes and appreciates that. It’s just refreshing,” Rory gushes. 

“And she knows how to scare off homeless guys!” Lorelai adds.

“I like to think she’s a weird mix of you, Lane, and Paris and maybe that’s why we get along. She really encouraged me to keep talking to you even when I was really mad.”

“Well then I really like this girl. What about Jess…tell me something about him.”

“I thought I told you a billion things about him already?”

“You spouted off weird facts in an argument. Really only one of them stuck…did Liz really try to name him after Jesus?”

Rory chuckled. “He was totally reluctant to tell me that, I told him he should expect some great gifts come Christmastime.”

“I always thought being a Christmas baby would suck, you’re competing with Jesus and Santa how the hell are you supposed to come on top in that fight?”

Rory shrugs. “He says he’s never been big about his birthday for that reason and then Christmas wasn’t big in his house because Liz was usually preoccupied with something else. I don’t know, I want to do something special for him when it comes around this year. Make up for all the birthdays he missed out on.”

“That sounds really sweet…as long as you two are still together.”

Rory glared in response. “Seriously mom?”

“What?” Lorelai replied innocently. “I’m just saying what if things don’t work out?”

“See you’re still doing it,” Rory argued. “You’re still acting like I’m making some huge mistake here but that’s not what’s happening.”

“So what is happening Rory, you still have yet to really tell me anything about this guy.”

“Ok fine,” Rory relents. “He’s been living in Philadelphia for a few years, grew up in New York with Liz. But he left at 18 and dropped out of high school to go find his dad who left him when he was a baby. Liz was always drunk, high, or with a new boyfriend so it wasn’t the greatest childhood. He ended up writing his first book when he was in California and made peace with his dad. He found Chris and Matt in Philadelphia and they published his book through Truncheon. Now he’s an editor there and is still working on his 2nd book. God mom he’s so smart, smarter than me even. He knows pretty much every book ever so it’s hard to one up him in a conversation about that and when he reads a book he writes in the margins and you can see all his thoughts and musings about the book. He could totally keep up with you and I in the movies and wit department, we’ll need to have him over for a movie night eventually. And he’s just…he’s really unpredictable sometimes, in a good way of course. He takes me on these adventures around the city and I don’t know what to expect. And he listens to me, really listens and he doesn’t judge me. He could have gotten so mad when I told him about Dean but he didn’t. He always says he’s done much worse in his life and it prepares him for stuff like this.”

“You told him about Dean?”

“Yeah, he wanted to know why I ran away. Thought it seemed strange.”

“Hm.”

“Yup. So that’s Jess. Anything else you want to know?”

Lorelai thought for a minute. “He’s not forcing you to do anything you don’t want to do is he?”

“Mom, no!” Rory sighs. “Not at all.”

“Like the night of his mom’s wedding, that wasn’t him taking advantage of some younger girl?”

“I knew what I was doing with him mom. And I wanted to. Look I realize that choice was incredibly strange and you have the right to disapprove of it because you’re my mom but I need you to understand that night probably saved me from a lot of grief regarding Dean.”

“What do you mean?”

“I just…meeting and being with Jess showed me there was just so much more out there for me. I had such a hard time meeting guys when I was at Yale, you knew that. And Dean was always there and he was comforting. I’d never been with a guy other than him you know? But Jess came along and changed everything and once he did I realized it would never work with Dean again. I moved past it.”

“Moved past it right into a make out session with him,” Lorelai responds sarcastically.

Rory rolls her eyes. “Here we go.”

“Well how do you explain that?”

“I made a mistake and put myself in a situation I shouldn’t have. But once I kissed him I knew for sure it was over and I let him know that.”

“Did you though? Because I’ve seen him around here since you’ve been gone and he pulled me aside once to ask where you went. I didn’t know what to tell him. He still seems to think he has a shot Rory and he’s still with his wife.”

“That is not my problem though, I told him I didn’t have feelings for him anymore!”

The two sat there silently sizing each other up, sensing they were a few words closer to being back at square one of their argument. They waited for who was going to cut in first and break the tension.

Lorelai conceded. “You’re right, if you told him you don’t feel that way about him anymore, he needs to respect that.”

Rory nodded. “He does. Maybe I need to write him a letter or something, tell him again, even tell him that I’m with someone else now. It’s never going to happen.”

“That might be a good idea,” Lorelai agreed. 

“Ok. I’ll do that tonight. Can you give it to him tomorrow maybe while you’re in town? I’m trying to avoid running into him while I’m here, makes it easier.”

“Sure, you give it to me tomorrow morning and I’ll be the messenger.”

Rory smiled at her mom’s acceptance. “Thank you. And I am sorry you had to see that mom. Both with Jess and Dean. But I’m growing up you know? And even though that’s happening I still need you. I still need my best friend and my mom.”

Lorelai hugs Rory and kisses her on her head. “That’s always nice to hear kid. I was beginning to think I’d become useless to you.”

“That could never happen mom,” Rory whispered. Lorelai stroked Rory’s hair and the two sat together comfortably for a few minutes. Rory looked up so she could see Lorelai’s face. “Hey mom?”

“Yeah?”

“When are you going to tell me all about you and Luke?” Rory asks coyly. Lorelai grins and releases Rory from her hug, immediately taking Rory’s hand and begins to gush about her own man.  
***  
It’s not until late Monday night that Rory is able to talk to Jess on the phone. 

They communicate through text over the weekend, both doing things that require their full attention. Jess is catching up on little things he’d been neglecting at Truncheon since Rory came in his life while Rory was making up for time lost with Lane and helping her mom and Sookie at the inn. They missed each other’s calls so they resorted to just texting, but this was the first chance they’d had to really have a conversation.

“It’s really quiet here,” Rory tells him.

“It’s really quiet here too,” Jess notes.

“No it’s not, you have the sirens and the couple down the block that fight all the time. I just have crickets!”

“Honestly? I don’t think I noticed before how much louder you make my apartment.”

“That’s really sweet.”

“Yup. How’s Stars Hollow though, really? How are things with your mom?”

“They’re going ok…getting better actually. She’s really come around about you and I now that I’ve told her all your great qualities. And I really explained the Dean thing to her too, we thought of another solution to his persistence.”

“He’s persistent?”

“He was asking my mom about me and where I was. When I’m coming back. So I wrote him a letter, I told him that it was definitely over and I regret that I kissed him that day. I told him about you and that I’m definitely with you and I don’t want to ruin that. He’d always be my first love and I appreciate the time we had together but it’s time to move past that.”

“Sounds like quite the letter.”

“I think it was! I had my mom give it to him so hopefully that’ll settle it. Anyway what’s been happening with you?” she asked curiously.

“It was a quiet weekend I guess. Caught up on all the work you actually have been distracting me from,” he teased.

“I do not,” Rory pouts. “I’d say you distract me more.”

“Mutually assured destruction I think. I did go out Saturday night with Matt and Chris, got some beers. Ama met up with us.”

“Oh yeah? How did the guys like her?”

“She and Chris were trading rap lyrics all night, they’re pretty much best friends. Matt was a little scared of her to be honest.”

“Scared?”

“Yeah. I asked him about it later and it’s just that he thought she was hot.”

Rory laughs. “She can be intimidating in this other wordly cool sort of way.”

“Yeah and Matt with his sweaters and button downs doesn’t think he can compete. Fun night though, we missed you.”

“I didn’t do anything that fun Saturday night,” Rory said sadly. “Now I feel like I missed out.”

“If it makes you feel any better, I didn’t have as much fun as I would have if you were there. And Ama complained about being the only girl.”

“That does make me feel better!”

“And I purposefully didn’t drink whiskey because I know how much you like it when I drink whiskey,” Jess slyly says.

Rory blushes and touches her face embarrassed even though Jess can’t see it. “I just like when you start rapping Biggie lyrics it’s fun!”

“And you like how much I want to touch you when I drink whiskey, while rapping Biggie lyrics.”

“Jess,” she hisses.

“Chills up that spine, that ass is mine,” he raps huskily.

“Stop!” she implores.

“Remember when I used to play between yo legs You begged for me to stop because you know where it would head, straight to yo mother’s bed.”

“You’re ridiculous,” she mumbles.

“Girl you look fine like a windface Rolex, you just shine, I like that waistline let me hit that from behind, which wall you wanna climb.”

Rory laughs at this point, because he’s right that she not so secretly likes when he does this. It was only a couple times but both were so silly and gave her a side to Jess that she didn’t at all expect. They were tucked in a booth at a dive bar not far from Jess’s apartment, heady and tipsy from a couple drinks when Big Poppa came on the speakers and brought a smile to Jess’s face. To her complete surprise he rapped along to the song. 

“You rap?” she asked surprised.

“Only Biggie honestly. He’s a New York institution,” Jess answered proudly.

She laughed and continued to listen, leaning into his embrace. His hand tightened on her shoulder and his hands skimmed playfully along her bare thighs. He whispered the chorus in her ear and she closed her eyes blushing. His hand creeped past the hem and into her panties as he rapped the song roughly in her ear. She let him keep going, totally enraptured and he continued to touch her after the song was over, kissing languidly until he made her come with a whimper.

“Is that making you hot?” he asks breaking her from her thoughts.

“A little,” she admits. “Not enough to do what you’re thinking of doing though, my mom is upstairs sleeping.”

“Oh so you’re getting ready for bed huh? What are you wearing?” he asks coyly.

She sighs. “Seriously?”

“Just go with it Gilmore, it eases the blow when I wake up tomorrow morning, reach for you, and you’re not there.”

She smiles to herself understanding that feeling. It was strange to sleep without him after she’s been doing it for awhile. 

“Fine…I’m wearing a tank top and shorts,” she concedes.

“Mmm those shorts I really like? That only just cover you enough to be appropriate?”

She wasn’t wearing those ones but he didn’t have to know. “Maybe.”

“Your ass looks really good in those,” he compliments.

“And what are you wearing?” she asks shyly. 

“Just my briefs.”

She closed her eyes and pictured him in the bed, lounging with the phone to ear lying on his back with a lazy smile on his face. 

“You painting a picture of that in your head?”

“Maybe.”

“Lot of maybes coming out of you Gilmore, you nervous?”

She paused. “Maybe…you know this isn’t my thing…”

“I’ll talk you right through it huh? Just like I try to with everything.”

“You do.”

“Are you lying on your bed?” he whispers. 

“I am.”

“I bet your hair is flowed around you like an angel, that’s how you always look to me at night. You know what I’d be doing to you right now if I was there?”

“What?”

“Sucking on your nipples through that tank top while you struggle not to moan too loud and wake up your mom.”

She gasps, feeling hot all over her body at his words. 

“I’d rather be with you in your bed,” she tells him.

“Mmm so you could be as loud as you want. But your childhood bed would be new, plus I know how hot you get when you think we’re gonna get caught.”

“Jess!”

“When I fingered you in the booth of that bar, you kept opening your eyes to make sure no one saw us but it just kept making you wetter honestly. I want to do that where you are right now, strip off your clothes and use my hands to make you scream. But you won’t so you’ll put your pillow on your face to hold it in.”

She couldn’t help how warm and wet his words were making her and the feelings they evoked. She slipped her hands into her shorts to lightly touch her clit moaning at the contact.

“Are you touching yourself Rory?”

“Yes,” she breathed. 

“Good, keep going, close your eyes, and pretend it’s my fingers. Pretend it’s me above you smiling.”

She could hear his breath get heavier and figured out he was doing the same thing as her. 

“Jess,” she gasped. “I wish you were here.”

“Wish I was too,” he strained. 

The two continued, Jess’s words and groans spurring Rory on, making her move her fingers faster against her clit. She inserted one finger in her core and was able to keep her rhythm, panting and moaning quietly. Jess’s descriptions were so vivid, telling her of fantasies he had of the two of them together, things they hadn’t done yet and she gasped assents when he asked her if she wanted that. She could feel herself coming and threw her face into her pillow to muffle her loud moans as she came. She could hear the same from Jess, his groans of satisfaction that she was familiar with ringing in her ear. 

They both came down from their highs, whispering their goodbyes since they felt the exhaustion of sleep starting to take hold. They slept easier that night than they had since they separated.  
***  
A couple days later, Rory is sitting in the kitchen organizing some leftover papers that were in her room when she hears the front door open and shut quickly. Quick heavy footsteps clang towards her and her mother appears frantic and worried.

“What’s wrong?” Rory immediately asks, stricken.

“I was just in town with Sookie and we saw Lindsay throwing Dean’s clothes out of the window of their apartment. You could hear her yelling at him and I kept hearing your name and something about the letter. I think she found it Rory.”

Rory’s face paled. “Oh no.”

“Oh yes,” Lorelai confirms. 

“Oh god she wasn’t supposed to see the letter! Doesn’t he know how to hide things?”

“Well what did you write in there? You never told me,” Lorelai says sitting down next to Rory at the table.

“I told him that I would always value the time we had together and he’d always be my first love but that it was over now and we had to completely move on. I regret that kissed me at the Dragonfly but it totally confirmed our time had passed. And I’m with Jess now and I really like him. So Dean needs to move on.”

“That sounds like a very good letter actually.”

“It is, but it’s still not good if Lindsay is looking at it.”

The two of them sigh and lean their heads on their hands, thinking of a next step. 

“Wanna go to Luke’s, eat our way out of this weird guilt?” Lorelai asks tentatively.

“We should take the back roads or something, who knows who we’ll run into.”

Lorelai shook her head. “No, no we’re not going to do that. It won’t do any good and it’ll take us an extra 10 minutes if we do that.”

Rory sighs in acceptance and gets up to go put on some shoes. The two women set off towards Luke’s with Lorelai’s arm around Rory in comfort. They walk in silence most of the time, taking moments to say hello to various townspeople that pass by. They’re almost in the clear, with Luke’s in sight when they see Lindsay and her mother come out of a store and come towards them. The two mother/daughter duos were similarly positioned, mother’s arms wrapped around their daughter as a source of protection and comfort. When Lindsay’s mother spotted Lorelai and Rory her countenance darkened and she marched up to them, Lindsay in tow, with determination. 

“How dare you show your face around here,” the blond woman hissed to Rory.

Both Rory and Lorelai looked surprised. “Excuse me?” Lorelai sputtered.

“You two are walking about here as if you haven’t ruined my daughter’s life! Dean is back home with his family and their marriage is ruined!”

Both women could say nothing to this, Rory biting her lip and looking down at her shoes. 

“Now hold on, Teresa I don’t think you know the whole story,” Lorelai tries to reason.

“I saw the letter,” Lindsay grounded out. “I saw it. I know you kissed him.” She looked at Rory with steely eyes. 

“No, Lindsay he kissed me. And once he did that I told him we couldn’t do that again. That was the last time I saw him,” Rory explains.

“Oh please! You’ve been chasing after him ever since he got married. You call him all the time, you tell him Lindsay is holding him back from his dreams and that she’s selfish. You’ve been planting seeds this whole time and you can’t pretend you haven’t,” Teresa yells. 

Lorelai goes to add to the conversation but Rory beats her to it. “You’re right,” she says softly. “I got in between your marriage a few times and I had no right to do that. But that letter was telling Dean that I am out of the picture. I’m really sorry Lindsay, you didn’t deserve that. He may have been my boyfriend first but he’s your husband.”

The group falls to silence but the looks of contempt on Lindsay and Teresa’s faces don’t change. 

“That doesn’t do me much good now Rory,” Lindsay says. “I probably should have known he was still hung up on you but you wouldn’t let go of him until you moved on. And now it’s at my expense. I guess you can dump this new guy and have him now huh?”

The blonde women hurry away leaving Rory and Lorelai stricken. Rory’s eyes fill with tears and she wipes them away from her face quickly and tells her mother she’s not hungry anymore. They turn away from Luke’s and hurry home, Rory trying to swallow down the cries building up in her throat.  
***  
Rory laid in her bed the rest of the afternoon crying with Lorelai at the head softly stroking her hair. The pain and guilt she felt in her gut were so crippling that the thought of eating sickened her when her mother offered to order them Chinese food.

“You have to eat something kid. This isn’t your fault?”

“But she was right,” Rory cried. “Maybe I didn’t realize at the time that’s what I was doing but I pursued Dean. I thought I owned him and I was selfish and now because of that Lindsay is so hurt. She really didn’t deserve that mom. Did you see her? She looked devastated.”

“She did,” Lorelai sadly agreed. 

“I really made a mistake. Running away to Philadelphia didn’t change that.”

Lorelai hummed in agreement. 

“I think I want to be alone. Don’t you have a date with Luke tonight?”

“Oh hun I don’t have to go on that, he’ll understand if I cancel-“

“No please don’t! I’ll be fine. I’m going to call Jess and then I’ll cuddle up with a book for the rest of the night. Go out with Luke.”

“Ok, if you’re sure. I was going to stay at his apartment too so I’ll see you in the morning?” Lorelai tells her reluctantly.

“Go. I’m serious,” Rory tries to smile to convince her mother.

Lorelai gives her one last smile of encouragement before she gets up to go get ready for her date. Rory burrows her face into her pillow and reaches for her cell phone on her bedside table. She hopes that Jess answers the phone. 

Thankfully he does on the 2nd ring.

“Hey!” he greets cheerfully.

“Hi,” she croaks out.

“You sound weird,” he immediately notices. 

Rory clears her throat. “Better?”

“Not really honestly. What’s up?”

“I have had quite a day actually.”

“Oh really, what’s the small town scandal of the day?”

“Girl finds a letter addressed to her husband from high school girlfriend and kicks him out of their apartment for the whole town to see.”

“Oh…shit.”

“Yup.”

“So she found the letter you wrote?”

“Sure did.”

“And then she kicked him out. Have you seen either of them?”

“I ran into Lindsay and her mom. It was pretty terrible.” Rory can feel the tears welling up in her eyes again, the heaviness in her chest returns. 

“Do you want to talk about it?” Jess asks sensing the heaviness in her voice. 

“It was really terrible Jess. And the most terrible thing is that she was right and I’m really selfish and a horrible person,” she tells him, the tears running down her face again.

Jess sighs. “That’s not true.”

“Isn’t it though? Didn’t I cause this by basically pursuing him and leaning on him for support when that wasn’t my right anymore? I made him think I wanted to try again.”

“Rory he was the one who was married. He’s the one who took vows to be faithful and loyal to his wife. Not you. Yes you made a mistake but in the end you’re the one who cut ties.”

“It doesn’t change that she’s really hurt and I caused that.”

Rory continued to cry and Jess rubbed his hands over his face, frustrated that he couldn’t do anything to help her over the phone. He hated seeing her cry. The only other time he had it was after a phone conversation with her mom. She looked and sounded like an injured animal that needed to be put out of its misery and he couldn’t really do anything to stop it.

“Rory please don’t cry,” he whispers. 

“I wish you were here Jess,” she cries. “Remember after that phone call with my mom? You just held me and read Proust. I really liked that, it helped.”

“Do you want me to do that? Read to you?” he asks hopefully.

“I just want you to be here. I really miss you,” she laments.

The two of them are silent for a beat. “I could be,” Jess whispers.

“What?”

“I could be there. I could leave now and be there by 10, 11 at the latest.”

“Jess you can’t do that!”

“I finished up a lot of projects at Truncheon this week, I can take the rest of the week off.”

“Jess please I can’t ask that of you. You can’t just drop everything because I’m crying. I swear I’ll be fine please don’t do that. I’m going to read and go to bed and tomorrow I’ll be editing the couple articles Matt sent me for the next Zine article. I’ll be so busy I won’t have time to feel sorry for myself.”

“Are you sure?”

“I’m sure.”

“Only if you’re sure.”

“I am. You’re really sweet though.”

“I try.”

She smiled into her phone, her tears starting to dry up. “Well you know what, I’m going to take a bath and then curl up with my book. I’ll talk to you in the morning?”

“Yeah. Feel better ok? I promise you you’re not a bad person.”

“If you say so.”

“I do…goodnight Rory.”

“Night Jess,” she said with a sad smile, wishing once again he were there with her.  
***  
Hours later she’s fallen asleep but is startled awake from incessant knocking on the front door. She shoots up and hurries to answer the door, not even bothering to cover up her skimpy tank top and shorts she’s wearing. It’s particularly hot in Stars Hollow tonight and even with the air conditioning it doesn’t make sense to knock much. She can’t imagine who would be coming to see her at this time.

She flings the door open and is surprised to see Jess standing there with a hopeful smile on his face.

“I didn’t believe you when you said you were fine,” he greets her. Rory is so shocked she doesn’t know whether to frown or smile.

“Jess…what…”

“This is what people in relationships do from what I hear,” Jess says. “You needed me so I’m here. Even if you said that you would be fine I thought it was important to make sure. Because you shouldn’t go to bed tonight thinking you’re a terrible person Rory, I don’t want to see that.”

Rory beamed and wrapped her arms around Jess, nestling her head in his neck. 

“You’re amazing,” she whispered. She reached back to look at him and kissed him hard, remembering that this is what she’d wanted all week, to be reunited with him. He fell into the kiss easily, wrapping an arm around her waist and another hand to her head, tilting it so he can deepen the kiss. Jess pushes her against the opening of the door and the two reacquaint themselves with their kisses for a few minutes, softly exploring their bodies with their hands. Jess breaks their kiss reluctantly, seeing the need for some air to his lungs.

“Is your mom home?” he whispers against her mouth. She shakes her head no. 

“She’s at Luke’s tonight.”

Jess smirks. “Lucky us.”

Rory breaks away and takes Jess’s hand to lead him into the house. He closes the door behind him and looks around in interest as Rory takes him to her room. He takes stock of shelves of books, the Yale paraphernalia, and simplicity of her childhood room. It was very Rory.

“Casa Rory,” he nods in approval. She blushes when she sees a couple teddy bears in the corner. She forgot about those.

“I just haven’t changed it very much since I was a kid you know?”

“I like it,” he says picking up one of her bears. It all fit who she was with him but also here in Stars Hollow. “So what were you doing when I came, reading? I don’t want to totally interrupt.”

“I was sleeping actually,” she says with an annoyed face. “But now I’m not tired anymore with all your ruckus.”

“Oh really? Well then I guess we could try and go to sleep,” he says with a wink. He takes off his white shirt and starts to unbutton his jeans, rolling them down to reveal his black boxer briefs. Rory’s mouth dries and gapes watching him toe off his shoes and kick his jeans off completely. He stands with his hands on his hips and an expectant smile on his face. “Ready for bed?” he asks.

Rory dumbly nods and follows Jess’s lead, getting into her bed. It’s much smaller than his in Philadelphia, and they have squeeze in to fit into the twin frame. She lies on her side and Jess gets in next to her, pulling her so that she’s half on top of him with their legs tangled. Rory sits up and leans her head on her elbow, looking down at Jess and tracing his face. He hasn’t shaved since she last saw him so there is a slight beard forming on his face she quite likes.

“Missed this,” she murmurs. He hums in agreement. He strokes her thigh and strokes her hair back with his hands and she closes her eyes in contentment. She gets down to his level again after a few minutes and snuggles into his neck pressing soft kisses. Jess smiles. “You’re wearing those shorts I really like, don’t think I didn’t notice.”

She smiles against his neck. “I’m surprised you haven’t done anything with that yet.”

He recognizes her challenge and takes his hand from her thigh to clench her ass in his hand. She gasps and laughs at him while he smiles roguishly. 

“I think I need to cash in on my childhood bed fantasy if you don’t mind Ms. Gilmore. We can just pretend your mom is here,” he winks. He turns over, lying on top of Rory, laying open mouth kisses on her neck. He nibbles at her pulse point earning a soft moan from her. She traces his chest down to the hem of his boxers and notices the bulge already forming there. She smirks.

“You really missed me,” she notes taking firm hold of his clothed cock. 

“God you know I did, wasn’t Monday night any indication?”

She nudges him with her free hand so that he’ll look at her and gives him a slow kiss. When she breaks she whispers, “Show me how much,” against his mouth. He grins against hers and agrees taking off her shorts and panties at the same time. They didn’t need foreplay tonight. Rory pulls down his briefs, first with her hands and finishes him off with her feet. They kiss wildly, Jess reaching up Rory’s tank top to cup Rory’s breasts and knead them. She pants against his mouth, reaching to clench his ass to bring his cock closer to her center. They moan together as he traces her outer lips and hits her center. 

“I need to get a condom, it’s in my pocket,” he gasps. 

“No I can’t…I can’t wait,” Rory pants. “You know I’m on the pill. Just this once, I need you.” She takes hold of him and wraps her legs around his hips to lock him in. Jess groans, honestly shocked at Rory’s boldness as she grasps his cock and pulls him slowly until he’s entered her. He breathes quickly, her bare vice grip taking him by surprise.

“Jesus Christ Ror,” he strains. 

“Oh my god,” she arches her back undulating her hips. Every time she’s with Jess is intense but this is beyond. Feeling all of him in her with no barriers is more than her body can handle in this moment. 

Jess takes hold of Rory’s hips and starts a fast pace, pounding into her. They’re both breathless, unable to breath properly. Jess sits up to be able hit Rory’s spots properly.

“Oh god,” she chants as he hits her g spot with every thrust.

“That’s right, you want it harder Rory? What do you want?” Jess grunted.

Rory arched her back further up, reaching her hand back to take hold of her headboard to ground her. Jess’s thrusts were relentless. 

“Please Jess, oh god.”

“Please what? Say it Rory, what do you want?”

“Make me cum! I’m so close, please!”

Satisfied with her answer, he begins a brutal pace and uses his thumb to press against her clit, stroking it furiously. The sounds he emits from her are almost ear piercing and he’s honestly thankful at this moment her mother isn’t home. It’s the loudest he’s gotten her to be. She’s shaking and crying out his name as she comes, and he keeps his pace up until he feels she’s gotten enough and is coming down from her high. He’s close and he pulls out quickly, stroking to completion and coming in spurts on Rory’s stomach. 

The two of them catch their breath silently, Jess reaching for tissues on Rory’s night stand to clean the both of them up. Once he’s done he leans down to give Rory a sweet kiss they both smile into, wrapping their arms around each other. 

“I’m really glad you’re here,” she says sleepily. “I’m really glad you didn’t listen to me. “

“I’m glad too. It was worth the drive.”

She smacks him playfully and they adjust themselves on the bed so that Rory is nestled against his side. She lays her hand on his chest and falls asleep contently to the feeling of him stroking her hair.  
***  
It’s like déjà vu a hour or so later.

Both Rory and Jess jump up, hearing frantic knocking from what sounds like the backdoor of the house. The two look at each other confused and Rory proceeds to jump up and put on her shorts that have fallen to the floor. Jess gets up as well, putting on his briefs and sits on the bed waiting and watching Rory hurry to the door and open it.

It’s Dean.

Rory’s eyes widen in shock and she blushes, knowing she looks ridiculously disheveled and her hair is a mess. Dean shouldn’t see her like this.

“Dean what are you doing here?” she exclaims.

“Look I saw your mom was with Luke tonight and so I figured you were alone and that I could talk to you.”

“Dean this isn’t…this isn’t a good time.”

“No I really need to talk to you, my life is totally in shambles right now. What the hell was with that letter?”

Rory crossed her arms over her chest protectively. “Seriously? You want to blame this all on me?”

“You didn’t have to write me that letter Rory. And I told you we could be together and I just-“

“You don’t get to put this on me,” She interrupts. “I made it clear in that letter that everything was done because you were still persistent. I know you’d been talking to my mom and asking her about me. Look I’m with someone else now and that’s not something I’m giving up. I’m really sorry about you and Lindsay but if you want to be with her I’m sure you can fix it. I took myself out of the equation though.”

Dean gives her a once over and recognizes that her disheveled appearance is not just from being asleep. The light pink glow is still present on her cheeks, something that happened to her quite often after a good round with Jess. “Wait a second, is he here? I saw a strange car out front,” Dean clenches his jaw.

“That’s none of your business Dean.”

“The hell it is!”

“You need to go,” she tells him firmly.

He moves to push past her but stops at the sight of Jess, casually leaning against the doorway of Rory’s room. At the sight of Jess’s own disheveled hair and only in his briefs, it was evident to Dean that Rory really had moved on.

“You heard the lady, she says you need to go,” Jess said coolly from his place. He was in no mood to forcibly get this guy out of the house but he would if that’s what he had to do.

Dean sighed, defeated and looked to Rory again. “Can we talk tomorrow at least?”

“No we can’t,” she said sadly. “It’s really over Dean. I’m sorry Lindsay found the letter but I meant everything I said. Please don’t make this harder.”

Dean stared into her eyes, wanting to say more but couldn’t find the words. He shook his head and stalked off into the night. Rory leaned against the doorway watching him go sadly. She wanted Dean to be happy but it wasn’t up to her anymore. She hoped he got the message. Once she saw he was gone she closed and locked the door and looked to Jess. She gave him a small smile and walked into his waiting arms, cuddling in his arms and accepting his comfort. 

“Now I’m really glad you’re here,” she mumbled.

“That guy really doesn’t take a hint huh?”

“Apparently not.”

Jess kissed her forehead and separated them so he could lead them back to her bed. She stayed put though and Jess looked back at her in confusion.

“I’m hungry,” she stated sheepishly. “I haven’t eaten since lunch!”

Jess chuckled knowing that was an absurdly long time for her. He walked past her to her fridge to see if there was anything edible for them to eat. With all the interruptions they’d gotten there’s no way they were sleeping much tonight. Might as well fill the time with food and making up for their separation.


	14. Chapter 14

**Notes for the Chapter:**

> Guys! This chapter was such a bitch to write I'm going to admit. There's something about writing them in Stars Hollow that was weirdly stifling. And that probably comes through in the chapter. It's also been a very busy week! Anyway, I'm nervous about this one so your feedback is seriously appreciated. Eventually once I'm done I'll be going through these chapters and reworking everything, fixing mistakes, etc so it's good to know what's working. Much love!

Lorelai pulled her jeep into her driveway, bopping around her seat to the music playing in the car. It was beautiful day, she had an amazing date with her boyfriend, and she didn’t have to be at work for another 2 hours so she could bug her daughter and treat her to breakfast.

Immediately her bright beam dropped to a confused frown, as her driveway was blocked with a car she didn’t recognize. Who was here?

She wracked her brain for a few minutes once she turned off the car, trying to place where she might have seen this car or who it could belong to. It looked too old to be Paris’ and it definitely wasn’t Lane…or Dean.

The only option was Jess.

Before the guy had…defiled her daughter….was that the right word to say? She didn’t know. But before then she had looked forward to meeting and getting to know Jess a little. He was part of Luke’s family and that was important to him. From the stories Luke had told her, his life sounded similar to hers in some ways. He’d been stifled in his own childhood with something missing the first chance he got, he left to figure out what he wanted and needed out of life. He struggled and worked and now he had reached some of his dreams. He was a published author. She would give him that credit at least, Luke had marveled that someone in his family was smart enough to do something so amazing.

He was just so much older and experienced than Rory. Luke hadn’t just told Lorelai the good things, he’d mentioned that there was a period of time Jess got into a lot of trouble and was almost going to be sent to Stars Hollow to “straighten out”. Unfortunately Liz herself was so out of it that she kept forgetting to lay down the law and actually send him. She knew her daughter, knew how careful and cautious she was about her life. It served her well up until this point…she just didn’t want to see her take a chance on this guy and regret it for the rest of her life.

She got out of the car and slowly made her way to the door preparing herself for what she was going to find when she walked in. She opened the door and quietly made her way towards the kitchen, listening in for any sudden noises she wanted to avoid. She turned the corner and stopped at the sight that met her.

Jess was sitting at her table in just a pair of jeans, sipping a cup of coffee, and lazily flipping through a magazine. She tiptoed to get a better look at him without alerting him of her presence. He seemed very at home in her kitchen, with one leg tucked under him and his head leaned on his bent hand.

“Hi Ms. Gilmore,” he said without looking up.

Lorelai stumbled in surprise and caught herself against the doorway. “Oh hey Jess what a surprise to see you here…in my kitchen…shirtless,” she stuttered.

Jess looked down at his shirtless chest and his cheeks turned pink. “Sorry about that…do you want me to grab a shirt, does this make you uncomfortable?”

It only made Lorelai uncomfortable because now she at least sort of got what made her daughter throw away her usual patterns for some time with this guy.

“No no,” she waved him off. “This is just an unusual sight to see in the Crapshack, not a lot of guys around here.”

“The Crapshack?”

“It’s what we call this house. It was a pretty apt description when we first moved in.”

“Interesting name.”

“We’re an interesting family, but I’m sure Rory has told you that.”

Jess nods. “She’s told me a lot of things.”

Lorelai raises an eyebrow and walks closer into the kitchen, dropping her bag on the floor and taking a seat across the table from Jess. She takes a look around the kitchen and takes a sniff.

“Did someone clean? This kitchen looks weirdly clean.”

Jess sputtered into his coffee and coughed to clear his throat. “Rory got hungry in the middle of the night…we…cooked.”

Lorelai stared at Jess and grimaced when her brain caught up to his double meanings. “Seriously? Is that what you came all the way up here to do?”

He at least had the decency to look embarrassed. “No, no that’s not what I came here to do at all.”

“Then why are you here?” Lorelai asked, her voice starting to become harsh.

“Rory called me last night and she was crying. She told me about what happened with Dean and his wife and I couldn’t let her be up here all alone when I knew how bad she felt about everything. So I came up here to make sure she was ok,” he explained calmly.

Lorelai’s face softened at his reasoning. “She called you crying?”

“She kept saying she was a bad person. When I offered to come up she told me not to but…when you’re in a relationship you make sure the other person knows for sure she’s not a bad person, even if she tells you coming to see her isn’t necessary.”

“That...that is true.”

“Ok…well that’s why I’m here.”

The two of them sat across from each other and examined each other with scrutinizing eyes, not knowing how to continue their conversation. They both knew this was their chance to make an effort for the sake of the girl still sleeping in the bedroom. They’d both been lectured about this, knowing there was still some animosity on one side and unwillingness to make small talk on the other.

Surprisingly it was Jess who cracked first.

“Look…first of all I’m not good at this. I don’t meet parents and I’m also not great at small talk. So usually I would be sneaking out the window to avoid having this moment with you but for Rory I’m going to sit here and try. Your daughter is really special and I’m not in her life to take her away from you or any of her dreams. She’s told me she wants to Christiane Amanpour someday and as long as she’ll have me, I told her she will be and I’ll always support her in that. And I want you to know that, because you’re her best friend and as happy as she’s been in Philadelphia with me I don’t think it’s complete without her knowing that she can talk to you. She may like me but she loves you. You’re her best friend. You’re her mom.”

Lorelai bit her lip to force back the tear coming up from her eyes. She refused to put down her guard and cry in front of this guy no matter how heartfelt and sincere his words were. He definitely was a writer.

“You seem to be doing ok with the small talk thing,” Lorelai joked. They both cracked a smile.

“She seems to really like you Jess. Thank you for not kicking her out on her ass when she first came to you at least.”

“It was easy, I was happy to see her,” Jess replied easily.

“You were?”

“Yeah…she’s…very cool Lorelai. You raised a very cool daughter,” he compliments.

“Ok you’re just sucking up now, stop.”

Jess raises his hands up in defense.

“You can make up for being so sappy by getting me a cup of coffee,” Lorelai orders.

Jess smirked and nodded in agreement, getting up and pouring Lorelai a cup from the coffee maker.

“Hey Jess,” she called.

He looked up at her in acknowledgment.

“Next time you want to make a good impression on your girlfriend’s mother, don’t have sex all over her kitchen the night before,” she said with a sickly sweet smile.

Jess looked away with a red face.

***

Getting a tour of Stars Hollow felt a lot different in the daytime.

The last time Jess was here, he got a tour but he certainly didn’t pay attention to his surroundings. It was dark and he was more concentrated on finding a place to be alone with Rory than to see what her town was about. He was kind paying for that now, walking hand in hand along the streets of Stars Hollow with Rory enthusiastically pointing out different sites with a story to go along with it.

“So this is Weston’s which has the 2nd best coffee in Stars Hollow, next to Luke’s of course. It has amazing pastries, we’ll have to have dessert there tonight maybe depending on when you go home. And during Christmas they have candy cane coffee and yes it sounds disgusting but it literally tastes like Christmas.”

Jess listens to Rory patiently and musters up a smile when her bright grin is directed towards him. Rory’s eyes narrow though when she zeroes in and immediately recognizes how uncomfortable Jess is.

“Am I talking too much? Oh no I’m talking too much,” Rory worries.

“No it’s not that it’s just…everyone is staring,” Jess notices shifting his eyes around.

Rory looks around and notices the various townspeople stopping to look from where they are at Rory and the new man in her life. She bites her lip in embarrassment. She’s so used to the freedom they have in Philadelphia that she forgets how scrutinized her life is in Stars Hollow. She can’t completely hate it, these people helped raise her and have shaped her life. She just wished they weren’t so interested in every small thing that happened, especially in her love life.

“Just…don’t worry about them. If you ignore them they’ll go away.”

“I think after the way you kissed me outside of Luke’s earlier, they think we’re the most interesting people in this town.”

Rory blushed at this remark. “I didn’t think about it!”

They continued to walk silently and Rory led him back to the bridge she’d shown him the night of Liz’s wedding. It became quieter once they arrived there, away from the shifting eyes of nosy townspeople. Rory sat down on the bridge and Jess followed her movements. They stared into the water, Jess rubbing his thumb over her knuckles, and Rory leaning her head on his shoulder.

“I used to come here all the time during high school,” Rory reminisced. “It’s basically the most private place in Stars Hollow so whenever everything got to be too much this was a really cool place to come and read or just think by myself. Especially after fights with my mom or Dean…especially after I broke up with Dean.”

Jess nodded. “I can see the appeal for this place.”

“Glad we could find a place that you’ll actually like in this town,” Rory smirks. She can tell that he’s impressed.

“It’s not Washington Square or Schuykill River Park but it’ll do.”

Rory smiles happily and kisses Jess on the cheek. “I’m really glad you’re here,” she says against it.

Jess smirks. “I couldn’t tell since last night, I’m glad you’re telling me.”

“Oh that round in the kitchen didn’t indicate anything to you?”

“No I’m mistaken, it was in the shower that sold it.”

Rory smiles dreamily, “I think the shower was your best work honestly.”

Jess laughs. “God, what are we going to do in August?”

“What do you mean?”

Jess’s face becomes more somber. “Think about it, we were away from each other for only a few days and I’m gonna be honest, it wasn’t fun. I had trouble sleeping because I was so used to you being there with me.”

“I did too,” Rory said glumly.

“But you’re going to have to leave in August and go back to school. So this whole thing between us….the being in same city thing has an end date.”

“You’re right. I haven’t wanted to think about it. Being in Philadelphia by ourselves has been a dream.”

“So what are we going to do? You not going back to Yale isn’t an option.”

“That’s true. So we need a plan.”

“I figured you would say that.”

“When we get back to my house we need to write down a plan. Especially because it’s almost like we’re addicted to each other. I haven’t slept well all week until you came here. I’ve never been like that! I was never addicted to Dean! So what will happen when I come back here full time? Will I go into withdrawals or something, I can’t afford that! Maybe we need to wean off each-“

“Rory!” Jess interrupts. “Take a breath, we’re not addicted to each other! We both have lives in our separate homes, even as it is we’re both pretty busy at Truncheon. And you’re just fine having girl time with Ama without me and I have the guys!”

Rory pauses thoughtfully. “That’s…that’s true. But maybe we should make an effort to spend nights away from each other. I can sleep over at Ama’s sometimes?”

Jess grimaced. “Are you serious?”

“Yes! What about the old apartment over Truncheon, Chris and Matt don’t live there anymore right? I can stay there sometimes.”

Jess sighed. “If you think that will be helpful.”

“I think it will,” Rory says determined. “I think we’ll be better off come August if we know we can stand to have time away from each other.”

“Well you think more about it and we’ll talk about it when you get back to Philly.”

Rory conceded and kissed Jess’s cheek again in reassurance. “We’ll be ok right?”

Jess nodded in response. Rory snuggled into Jess’s embrace and he wrapped his arm around her.

“Hey Rory?”

She looked up into his face curiously. “What’s up?”

“Since we’re having an honest conversation and all…we need to talk about last night.”

Rory sat up alarmed. “What was wrong with last night?”

“Nothing was…wrong necessarily it’s just…when I first got there and we had sex you didn’t let me put on a condom.”

“Oh.”

“We’ve never talked about birth control before.”

“I…I am on birth control, I’ve been on it since I was 17,” Rory says defensively.

“Ok but I didn’t know that. And it’s not your fault we had sex without a condom last night but if we’re going to do that we have to be super careful you know?”

Rory pulled away from Jess and crossed her arms over her chest protectively. “You were mad that I did that?”

“No I’m not mad…it just surprised me.”

“Oh because I’m so innocent and inexperienced?”

Jess rolled his eyes. “Where did I say that Rory?”

“I thought you would have appreciated that. That I wanted to be so close to you?”

“It’s not that I don’t appreciate it, it’s that if we appreciate it too much and we’re not careful you’ll get pregnant!”

Rory is shocked. “Oh really?”

“Yes really…say you get sick or you take antibiotics or something. It’s not 100% effective Rory, it’s why we need the condom.”

“This is a ridiculous conversation.”

“No it’s not and you know it isn’t.”

Rory rolls her eyes and gets up. “I’m not going to get pregnant just because of the one time we had sex without a condom on. Maybe I need to go back to my house and take all those birth control pills I’ll forget to take.” She storms off without a look back, leaving Jess in a state of puzzlement.

***

The main problem with Jess’s argument with Rory is that it happened here in Stars Hollow.

 

They were always bound to have an argument. Jess supposed that things were too smooth sailing over the time they’d been together and they were due for a fight of sorts. He just wishes it didn’t happen in a town where he really only knows 3 people.

 

Going back to the Gilmore house was out of the question since Rory seemed to be pretty mad. It seemed best to just let her have some time to cool off. The only other place he knew to go to was Luke’s. He had just eaten breakfast there with Lorelai and Rory earlier, but he supposed he could go back again and wait it out without any suspicions. He was going to have to drive back to Philadelphia tonight anyway since he had to be at Truncheon for some meetings in the morning.

 

He walked back through the unfamiliar path until he found the town square again. He was glad the town was so small that it was hard to get lost in terms of finding your way around to the major stores. All you ever had to do is make sure the Gazebo was still in sight. Jess avoided the confused looks of the townspeople who had just seen him with Rory earlier. Everyone was scrutinizing and smart enough to figure out that him walking around without Rory was probably not a good thing. He kept his head down and hurried his steps.

 

When he walked through the door of the diner and bell chimed, he was grateful to see that he was finding refuge during a lull. Only the strange man named Kirk who seemed to ask a lot of weird questions both times he was here happened to be sitting at a table in the corner by himself. Luke was nowhere to be seen, but there was an asian girl standing looking bored behind the counter.

 

This must be Lane.

 

Rory had talked a lot about her best friend and the ways she valued their time together in Stars Hollow growing up. He knew vividly about the conflicts concerning Lane and Mrs. Kim growing up and how they were slowly making amends. Rory had also informed Jess about Lane’s musical aspirations and tastes, and this fact alone was enough to say he could carry a conversation with the girl.

 

Lane noticed him standing there and quirked an eyebrow at the presence of someone she didn’t know at such a quiet time of the day in the diner.

 

“Can I help you? Are you new in town?” Lane questioned. Jess walked over to the counter and took a seat at one of the stools.

 

“You could say that,” Jess answered vaguely. “Just some coffee for now would be good.”

 

Lane gave him a nod and filled his order, pouring him a cup of coffee in a big cup and placing it in front of him. Jess smiled to himself, recognizing this was the size Lorelai and Rory lived on this morning. When Luke brought them regular sized cups, they both looked at him as if he’d grown two heads. However the thought of Rory made his smile dim, remembering the argument they were in. Unfortunately it was times like these that Jess recognized that Rory was younger and less experienced than he was. Maybe he pushed her too much sexually, far from what she was ready for if she couldn’t have these conversations with him. But it didn’t change that he liked her a lot.

 

“Anything else I can get you?” Lane cut through his thoughts with another question.

 

“No,” Jess answered morosely. “Just the coffee is fine.”

 

Lane put the coffee pot back and continued to look curiously at Jess. There was something about him…

 

“You look familiar for some reason,” Lane observed.

 

Jess raised his eyebrow. “Huh.”

 

“Do you have family here?”

 

“Yes...not very close but they’re family.”

 

Lane continued to think for a minute. “Is this going to be a guessing game? I’m not really into guessing games.”

 

“Aw come on, what else do you have to do around here?”

 

“I’d really rather scrub this counter than play a guessing game with you. What’s your name?”

 

Jess paused, knowing for sure that once he gave up his name the jig was up and Lane would know exactly who he was. But so far he liked Lane...he’d bite.

 

“Jess,” he answers with a smirk. Lane’s eyes widen at this revelation.

 

“Oh my god!” she exclaims pointing at him. “You’re Jess.”

 

“Sure am.”

 

“You’re Rory’s Jess!”

 

“I don’t know if she would claim me if you asked her right now but yeah I guess I am.”

 

Lane ignores this piece of information. “She could not shut up about you when we hung out the other day and now I kind of get why.”

 

“Thank you?”

 

“It’s definitely a compliment. What are you doing here?”

 

Jess shrugged. “I heard Al’s Pancake World was having international cuisine grab bag night and I couldn’t resist.”

 

“Oh, don’t be disappointed, he always picks the international cuisines he’s really bad at making so it’s a lose/lose situation all around.”

 

Jess rolled his eyes. “All that for nothing, I was hoping for some greek.”

 

Lane giggled. “But seriously, did you come to see Rory?”

 

“I did, she had a weird confrontation with that ex and his wife and she was pretty down about it. Wanted to make sure she was ok.”

 

Lane put her hand over her heart. “Oh that’s so romantic! And wait I heard about the Lindsay thing, that got around town but Dean too?”

 

Jess grimaced. “Maybe you should talk to Rory about that, it sounds more like girl talk.”

 

“Oh...where is Rory?”

 

Jess paused. “I’m...I’m not sure.”

 

“Why wouldn’t you know where she is, you’re visiting her?”

 

“Well...she’s not very happy with me right now,” he stated vaguely.

 

“So you’re in a fight?”

 

“If that’s what they call it…”

 

“What did you do!?” Lane exclaimed, getting defensive of her best friend.

 

Jess put his hands up in alarm. “I didn’t do anything, I just tried to have a talk with her about something and she got mad.”

 

“Rory doesn’t mad about things,” Lane scoffed.

 

“I can tell that already but she’s mad at me and I’m not sure what to do.”

 

Lane relaxed her stance seeing the conflicted look on Jess’s face. “Well...why did she get mad?”

 

Jess hesitated. Rory probably wouldn’t appreciate him telling her best friend all about their issues with protection. How could he frame this?

 

“I don’t know how much I should tell you...I think she thinks I throw my older age in her face?”

 

“Well do you?”

 

“No! If I thought her being younger than me was a problem I wouldn’t be seeing her. That doesn’t matter to me.”

 

“So then why would she be mad?”

 

“I don’t know...you’re her best friend!”

 

Lane smirked and thought to herself for a few minutes. Jess sipped his coffee nervously, hoping that Lane would have some insight.

 

“Rory is a bit of a know it all sometimes,” Lane notes. “She really thrives off of being the best and knowing a lot of things. She’s really quiet about it though, more so than her friend from school Paris. But she’s not used to being the one that doesn’t know something...she never had to do that with Dean. So maybe it’s something about you being older, about knowing more about something than she does that makes her uncomfortable?”

 

“That...could be part of it.”

 

“What do you think you’ll do now?”

 

“Well I don’t know. Should I even show up to her house? Would she want to see me?”

 

“She can be pretty stubborn when she’s mad at someone,” Lane agrees.

 

Jess sighs in defeat. “I want to just go and talk to her later but...that doesn’t sound like a good idea.”

 

“It’s not,” Lane confirms. “Leaving without saying anything to her will definitely make her more mad.”

 

“Seems like the easy way out.”

 

“It is. Rory told me you’ve had only one other girlfriend right? So relationships aren’t your thing.”

 

“You are correct.”

 

“So this making up thing isn’t coming easily to you huh?” Lane realizes. Jess simply nods.

 

“Well at least you’re still here and you’re trying to figure out why she’s mad,” Lane encourages. “Look she seems to really like you. I’m sure if you apologize and you bring her some coffee from Lukes along with one of these donuts you can bribe her into forgiving you.”

 

Jess looked over at the case of donuts with interest. “Glazed or Jelly?”

 

“I would take both. And an extra if Lorelai is there,” Lane winked.

 

“Well then, I’ll take two coffees to go and 2 glazed and 1 jelly donut,” Jess decided. Lane got to work packing up Jess’s order and once she was done she handed it to him with a smile.

 

“It’s on the house,” she insisted. “Unless you make her more mad then I’ll just come find you and make you pay.”

 

Jess smiled gratefully. “I appreciate that...and your insight. Rory has told me a lot about you and I think it lives up to the hype.”

 

“Same here,” Lane grinned. “I’m sure you guys will work it out. And next time you come to visit we have to discuss the punk rock scene in Philadelphia, I’m super curious. Rory told me about the bar you guys went to that had that punk 80’s night it sounds amazing.”

 

“You should come visit before the summer is over, check it out yourself. Lots of cool shows all the time in small venues. Rory would love that.”

 

Lane vehemently agreed. “I think I will! I’ll talk to her about it.”

 

Jess gave her a nod and a small smile and took one last sip of his coffee. He waved his hand and gave his thanks and walked out the door into the mid afternoon sun of Stars Hollow. Hopefully Lane was right and donuts would smooth over these edges.

 

***

Rory wasn’t sure what was wrong with her.

 

Usually when she and Dean had a fight she could easily pinpoint how and why it started. Even if it was something that was her fault, she was able to realize that pretty quickly into the argument based on Dean’s level of frustration. But Jess...Jess was so cool and collected most of the time that they didn’t need to fight. The only other time she’d been frustrated with him about how much contact he kept with her during the day he was able to realize pretty quickly and fix the situation.

 

But Rory knew this one was kind of on her. She just didn’t know why she was so mad.

 

Not using a condom the night before was such a spur of the moment decision. She always felt out of control when she was with Jess, her inhibitions completely put to the wayside. For how shy she was as a person she felt like she could be bare with Jess in a way she wasn’t with most people...so why not be bare with him physically? She was responsible and she took her birth control everyday without fail since she started having sex with Dean. She just never felt the need to do this with Dean. Not like with Jess.

 

So to hear him almost reprimand her for doing that was insulting and embarrassing. Their age difference didn’t matter to her most of the time, but he lorded his experience over her as if she was a dumb kid that didn’t know any better.

 

She huffed all the way back to her house once she left him, not caring if he followed her or not. When she got back to the house she slammed the door and let out a frustrated sigh, moving into the living room only to become startled by the presence of her mother.

 

“Mom!” Rory jumped. “Aren’t you supposed to be at the inn?”

 

“Nah,” Lorelai waved off. “Michel and I decided he could handle things there for the day so I came back.” Lorelai looked and noticed that Rory was by herself. “Where’s the boy toy? Did he go back to Philly already?”

 

Rory frowned. “I don’t know.”

 

“What do you mean you don’t know?”

 

“I left him at the bridge, I don’t know what he’s doing!”

 

“Ok I’m confused why did you leave him at the bridge?”

 

“We got into an argument ok?” Rory exploded. She came to sit down next to her mom with a sad look on her face.

 

“I don’t know what’s wrong with me. It’s just...him being older usually isn’t a problem but it’s like he was telling me that I was stupid and this is how it has to be from now on.”

 

“Ok I’m missing something, what were you being stupid about?”

 

Rory blushed, knowing that if she wanted to vent to her mother she was going to have to tell her the whole truth. “Well you see...when we were alone here last night...we…”

 

“You had sex,” Lorelai finishes easily.

 

“How did you know?”

 

“Uh kid...you had sex in our kitchen. Our kitchen is never that clean and Jess’s guilty face when he saw me this morning gave it away.”

 

“Ugh. I don’t want to talk about this with you.”

 

“Why do you think I’m going to judge you?” Lorelai challenged.

 

“Yup.”

 

“Well how about if I promise not to?”

 

Rory waits a beat. “If you do, we go to Al’s tonight.”

 

“Ah not tonight!”

 

“Final offer m’am.”

 

“Ok ok fine. Now what’s going on.”

 

Rory took a deep breath. “So...we did...stuff last night and well one of the times-”

 

“One of the times?” Lorelai asked incredulously. “How many times were there? Oh god wait don’t tell me.”

 

“Mom!”

 

“Whatever it’s not judging! I’m just surprised!”

 

Rory rolled her eyes. “Anyway one of the times I asked him not to use...protection. Insisted you could say? I don’t know it all happened very fast.”

 

Lorelai took a deep breathe and tried to school her features to remain neutral. Her thoughts were racing with all sorts of thoughts, one of which calculating how long it would take for that emergency contraception pill she’d heard about to officially become available. They could take one that’s in early development right?

 

“Oh,” Lorelai managed.

 

“And look, it seems irresponsible but you know I’ve been taking pills for awhile now so I didn’t think it was a big deal. But today he did and he made me feel really stupid about it. As if I don’t know the risks, who does he think I am!?” Rory huffed.

 

Lorelai stared straight ahead, avoiding eye contact with her daughter so that she wouldn’t say everything that was in her head.

 

“That sounds...really frustrating,” Lorelai tried to empathize.

 

“It is! I more than anyone does not want to get pregnant, imagine how bad that would be. I would have to drop out of Yale, grandma and grandpa would probably have heart attacks, and you would be so disappointed. Right?” Rory looked to Lorelai pleadingly. The more she talked, the more unsure she became of the situation. Because Jess was right...getting pregnant would be bad.

 

“Well...I…”

 

“Wait, mom...please play the mom card...I think I need the mom card.” Rory decided.

 

“Are you sure?”

 

“Please? But not too harsh?”

 

“Ok...well...I hate to say it but Jess is right. I know things can get overwhelming and it probably feels...good...but it wouldn’t feel good if you got pregnant right?”

 

Rory shook her head.

 

“Look kid, this is the reality of being in a relationship with an adult who has experience. He was trying to protect the both of you. If you’re going to do something like that you need to have backup. Otherwise you need to keep those rubbers handy at all times...and the pills. Do you get that?”

 

“I think so,” Rory mumbled.

 

“Good. So what are you going to do about Jess?”

 

“I should probably find him and apologize. God I’m so stupid, why did I freak out so much?” Rory lamented.

 

Lorelai sighed. “To be fair, there’s high expectations around here when it comes to pregnancy. At least you wouldn’t be 16 and pregnant if it happened!”

 

“Oh god don’t say that! I’m **not** going to get pregnant. I promise.”

 

Lorelai smiled sadly. “That’s really sweet of you to say but you can’t promise me that kid. Just be careful.”

 

“I can promise you that and I will. I’ll be extra careful from now on,” Rory insisted.

 

Lorelai swallowed down whatever extra judgments she had, trying to respect Rory’s wishes. Rory smiles gratefully and gives Lorelai a big hug.

 

“That was a pretty good mix of the mom and best friend card I have to say,” Rory compliments.

 

“Thanks kid, I guess we’re both learning.”

 

They separate and Rory stands up and brushes off her jeans. “I’m going to look for Jess and apologize. Hopefully he wasn’t so freaked out by me that he ran back to Philadelphia.”

 

Lorelai waves Rory off and she walks quickly to the door to look for Jess. Rory opens the door and stops in her tracks since Jess is blocking the doorway. He’s balancing a tray of coffee cups, a bag from Luke’s on one hand and trying to knock on the door with the other hand.

 

“Hey?”

 

“Hey!”

 

“You...have a lot of stuff there in your hand.”

 

“Just some more coffee...and donuts for you and your mom. Figured you needed a re-up.”

 

“Did someone say donuts!?” they heard Lorelai yell. “Did you bring jelly?”

 

“Yup,” Jess yells back.

 

“Oooo,” Lorelai cooes. “Rory I think I like him now!”

 

Both Rory and Jess laugh and Rory allows Jess in so that he can give Lorelai the donuts and coffee. Rory stays by the entryway of the living and giggles watching Lorelai tease Jess about how great he is.

 

“Oh Jess you’re so dreamy,” Lorelai cooes in an exaggerated voice taking a jelly donut out of the bag and eating it. Jess looks to Rory in alarm and she gestures for him to follow her outside. Jess waves to Lorelai and follows Rory out to the front stoop. They sit on the steps and look at each other expectantly.

 

“I’m sorry,” they say at the same time. A smiles grows on both their faces.

 

“I’m a crazy person,” Rory tells him. “I’m really sorry. You were right. I was being totally irresponsible and we need to think about being protected. You’re so right.”

 

“Rory stop, you’re not an idiot,” Jess puts his hand on Rory’s knee to calm her. “I don’t want to make you feel like you’re stupid just because you’re younger than me. That’s not how I really see you. I mean...you know more about this relationship stuff than I do. You’re teaching me a lot.”

 

Rory beams. “I am?”

 

“You know you are,” Jess scoffs. “I don’t know anything about this shit so you need to tell me when I’m doing it wrong.”

 

“And you know the physical stuff isn’t my forte...and I trust you not to take advantage of that.”

 

Jess leaned over and placed a short, sweet kiss on Rory’s lips. “I won’t,” he whispered against it. Rory leaned over to give him a big hug.

 

“Well we got through our first fight. And you brought donuts to apologize! So you’re totally getting the hang of this.”

 

“You can thank Lane for that actually.”

 

“You met Lane!?”

 

“I did. She’s pretty cool, I told her she should visit us in Philly while you’re still there.”

 

“Oh that would be so fun! I totally want her to meet the guys and Ama. And to see the Magic Gardens and a show at the Troc. She would love the TLA!”

 

“Slow down Gilmore, we’ll get there,” Jess reassures with a laugh. Rory blushes.

 

“So look I hate to cut this make up short, but I have to get on the road soon. I have meetings tomorrow,” Jess said regretfully.

 

Rory’s face fell. “Oh god I was such an idiot that I missed the rest of the day with you!”

 

“Hey it’s fine, you’ll be back on Sunday right? And this fits with your weaning off plan right?”

 

“I guess,” Rory mutters. “I just don’t want you to go.”

 

Jess lifts Rory’s face and kisses her cheek before giving her another sweet kiss that brings the grin back to her face.

 

“Sunday I’ll show you what make up sex is all about,” Jess winks. “Don’t be late.”

 

“Oh I won’t. We have so much to do! And I have so much to catch up on at Truncheon, I owe Matt like three articles for being gone all week! And then we’re going to the beach next weekend and eating all the pizza, hot dogs, and salt water taffy we can find! I definitely won’t be late.”

 

“Good...because the rest of this summer would kind of suck without you.”

 

Rory pats Jess’s cheek affectionately. “Yeah yeah...I’d miss you too.”


	15. Chapter 15

**Notes for the Chapter:**

> We’re back in Philadelphia! This was miles easier to write than the previous chapters. Something about Stars Hollow is very stifling for me when writing these two.

 

Working at Truncheon was completely different from working at the Yale Daily News for a number of reasons.

 

Matt was certainly more level headed than Doyle. And Doyle’s criticism of her work had been hard to adjust to at first but it proved to be incredibly helpful by the end of her freshman year. Matt was fun though and took the time to really teach Rory about the ins and outs of how a magazine can be really similar and different from a newspaper. It was a lot more opinion based, and it was hard for Rory to adjust to giving her own opinion in some respects. It reminded her of the reviews she did for the Yale Daily News. She told Matt about the ballerina fiasco and how it made her afraid she would go too far in her writing. Matt was understanding though and gave her good advice about her obligation as an author towards those she’s writing about.

 

“I mean here’s the thing Rory, there’s a difference between doing a review of someone’s work and then doing an interview. A review is supposed to be an honest piece on your opinion of whatever work you’re viewing. All the reviews you do should be coherent enough for consistent readers to understand your voice and the way you view art. So the ballerina’s performance didn’t move you-it’s not on you to apologize for that even if it hurt her. It would be a little different if you did an interview with her that seemed pleasant but then you wrote a scathing article about her. Now that would seem low down and dirty. Just remember that around here.”

 

It was helpful for Rory moving forward as she started to write more pieces for Truncheon. Matt was pretty relaxed on what he had Rory write about as time went on. He gave her some assignments and ideas but he also encouraged Rory to take some initiative and think of something on her own. She’d found some inspiration but not much...and it was beginning to worry her.

 

“I really need to buckle down for the zine,” Rory told Jess as she paced his apartment that afternoon after returning from Stars Hollow. “I’ve been doing really great with some of the editing and layout stuff Matt has me doing but I really need to step it up creatively. I’ve got no juice!”

 

“Matt seems pretty happy with your work so far,” Jess encouraged. “He said something about how even though you were gone all week you were super productive with the layout before you left and really helpful with copy editing remotely this past week. Says you’re really reliable.”

 

“But it’s not enough! I didn’t expect to get this gig so I feel like I need to blow him out of the water. What do you think? What does he want me to write about,” she questioned facing Jess.

 

“I can’t tell you that.”

 

“Why not?”

 

“Because I don’t know what he wants you to write. We’re keeping all of that pretty separate. I haven’t worked on the zine in awhile because it’s Matt’s thing. And we decided once he took you on that having me involved in any way would be too convoluted.”

 

“Oh.”

 

“Yeah.”

 

“So you’re useless to me?”

 

“Pretty much.”

 

“Well what am I supposed to do?” Rory asked exasperated. “We’re in July and time is going fast. I need to have a good project to give him. Especially if I’m going to the beach with you next week. He’s being super nice about that by the way.”

 

“Yeah I may have begged and pleaded about that.”

 

Rory scoffed. “Only because it benefits you too.”

 

Jess rolls his eyes. “Well yeah. You and me in a house on the beach all week by ourselves? You in a bikini walking around? Of course I begged him to give you another week off no questions.”

 

Rory blushed. “A bikini?”

 

Jess raised his eyebrow in confusion. “Why? Is that weird?”

 

“I just...I don’t own any bikinis.”

 

“Oh...well do you want to?”

 

“I don’t know? Do you want me to get one?”

 

Jess hesitated. “No...because it doesn’t seem like you want to.”

 

“It’s not that I don’t,” Rory defends. “I just never had one before. Even when I went to Florida for spring break I wore my usual one piece. I felt weird about getting a bikini. And I don’t know why...will I look good in one-”

 

“Oh don’t worry about that, you’d look good in one,” Jess interrupts with a wink.

 

“You’re just saying that.”

 

“I’m not! You know by now I don’t do that.”

 

Rory frowns. “You’re right. Maybe I’ll see what’s out there...if there’s anything I like...doesn’t hurt to try something new I guess.”

 

Jess shrugs. “Only if you like it and feel comfortable in it. Won’t be fun watching you run around the beach in a bikini all week if you’re not feeling good in it.”

 

Rory hums in appreciation. “You’re sweet.” She goes to Jess’s place on the couch and straddles him, making sure he’s securely between her legs. She grabs his face gently and gives him a slow kiss that makes him groan.

 

“You know,” she whispers once she breaks their kiss, “i’ve been back for a couple hours now and I still haven’t gotten a proper welcome or that make up sex you promised. You’re a bad boyfriend.” She pouts and he lets out a big laugh.

 

“Oh I’m a bad boyfriend?” he challenges. He grabs both of her legs and lifts her up with him off the couch, carrying her to his bedroom. “How about you teach me how to be a good one huh?” She giggles in response and kisses him fiercely as they enter his bedroom and fall on his bed together.

* * *

Rory was especially determined to be more productive than ever at Truncheon once the week started. 

 

She got up before Jess did, forgoing their usual morning talk before they started their day. She left him a note of apology but that she would certainly try to make it up to him later that day by buying him lunch. She got to Truncheon before any of the boys, organized her desk and got to work sifting through the submissions Matt had sent her during the week but that she didn’t have a chance to look through. She wanted to have solid answers for him on what pieces they should be putting in the issue by the time he walked in the door. She made a pot of coffee that would last long enough for when the boys walked in as well. 

 

Matt arrived first and was pleasantly surprised to see Rory already deep into her work. He greeted her and asked about her time at home and if she’d been able to take a look at the submissions he sent her.

 

“I just looked them over again actually,” Rory confirmed. “I’ve separated all of them into a Yes, No, and Maybe the next issue pile if you want to take a look?”

 

Matt grinned and went to see Rory’s progress. She smiled proud of herself as she continued finishing the edits on a piece one of the freelance writer wrote. 

 

“Hey Matt,” she called out. “Can we talk this afternoon about the next issue? I’m having trouble finalizing some ideas,” she asked.

 

“Sure! I actually wanted to talk with you too about the next issue. Let’s talk before lunch,” he answered. He got himself some coffee and went into his office leaving Rory alone in the main room.

 

Jess and Chris arrived together 30 minutes later talking and laughing together. Chris greeted Rory with a wave and a smile before going into his office and Jess greeted Rory with a kiss on the forehead. 

 

“You were gone before I woke up this morning, you usually don’t do that.”

 

“I know, I wanted to get a head start on things since I’d been gone all last week and it’s good! Shows Matt I’m committed. We’re going to talk before lunch about ideas for the next issue.”

 

“Oh so you got some inspiration?”

 

“Nope. Hoping that talking with Matt will help. If I know what direction he wants to go I can kind of go from there.”

 

Jess frowned at this revelation, but pushed down his need to warn Rory by mustering up a smile and kissing her cheek. “I’m not sure whether or not that’ll work but I hope you end the meeting with some good ideas. Look I’ve gotta go call that writer in Denver we’ve been trying to pin down but I’ll see you for lunch ok?”

 

Rory nodded in confusion and watched Jess go into his own small office. She shrugged before going back to her own work.

 

The morning passed quickly with Rory able to finish up sending out emails to submitters who they were not going to include in the issue and all her copy edits. She’d even been able to think of a couple ideas for articles she could write for the next issue, but she was still unsure about how good they were.

 

It was close to 11:30 when Rory walked by Matt’s office and saw that he didn’t look too busy. She shyly knocked on his door and asked if she could come in.

 

“Sure, take a seat Ror,” he waved her in.

 

Rory eagerly sat down and laid out her notepad with her ideas. 

 

“Ok so I’m thinking for the next issue we had a lot of submissions that were a little more political than usual which is kind of cool. Those comics we got about the war? Maybe a story on how artists in Philadelphia are taking a political stance, especially in the birthplace of America?”

 

Matt nodded, thinking deeply about Rory’s suggestion. “Well sure that could be a good idea. Maybe send that over to Clara she would definitely be able to make something out of that.”

 

Rory frowned. “Oh...you want Clara to write this? I thought...I thought I was going to.”

 

“You could but I can already tell you don’t really want to.”

 

“How can you tell?” Rory asked defensively.

 

“Also I wanted you to focus on a specific project for the rest of the time you’re here. Remember we talked about that? Something that’s all your own, featured in every zine? You’ve done a really great job here so far Rory and the pieces you’ve written have been good. I think they just lack in your distinct voice as a writer which is because you’re not devoted and interested in it the way you should be.”

 

Rory bit her lip. “What do you mean you can’t tell my voice?”

 

Matt leaned into his desk, folding his hands. “You’re a great writer and the pieces don’t lack in the information but reading the few pieces you’ve done the tone you take is always wildly different. It’s almost like you’re trying to emulate someone else every time. I didn’t notice it until I took a look at all your articles so far. So I want you to focus on figuring out a project that is all you and really encapsulates your voice as a writer. Does that make sense?”

 

Rory nodded, avoiding eye contact and fiddling with her pen. Matt noticed her discouraged countenance and sighed. 

 

“Hey, don’t worry about it. Do you have any other ideas about what that might be? I’m sure you’ve been thinking about it.”

 

Rory’s breath hitched and her cheeks reddened. “I...um...honestly I don’t have a clue.”

 

Matt raised his eyebrows. “Ok...well can you have an idea by the end of the week? I want this to be something substantial for the zine.”

 

Rory nodded in agreement and quickly got up to go back to her desk. When she walked out of Matt’s office she looked to see the door to Jess’s open. He looked up at her from his desk and saw her conflicted expression. He mouthed, “Are you ok?” to her and she shrugged in response as she dropped her notepad on her desk and heavily sat down in her chair. 

 

She’d have to cancel lunch. She had a lot of work to do.

* * *

A couple days later Rory had no good ideas, so she decided to pour all her productivity into finding a bikini for the beach with Ama.

 

She really had been planning on buying something new anyway, it had nothing to do with Jess. She’d almost forgot to grab her usual one piece when she was home in Stars Hollow but once her mother had seen her pulling it out to put in her suitcase she’d teased and made fun of her for still having that thing and daring to wear it in front of her boyfriend.

 

It ended up staying put on her bed.

 

So she walked around the liberty place shoppes with Ama trying to muster up the enthusiasm her friend seemed to have for this endeavor. Ama apparently loved bikinis but that was probably because she had great boobs, a full, curved figure, and an amazing skin tone that would look good with most colors. Despite her time in the sun Rory was still pretty fair but Ama tried hard to make her see that was a good thing.

 

“Rory I have no idea what you’re worrying about,” Ama commented. “Has Jess ever told you that you have a great ass? Because you do. And if he hasn’t told you I might have to smack him next time I see him.”

 

Rory shrugged glumly. “He’s told me a couple times I guess.”

 

“Well good! You have good hips too which is honestly essential to having a good ass so I think a string bikini would accentuate all of that more. Trust me when we find you something good, Jess won’t know what to do with himself all week.”

 

Rory obediently followed Ama around Victoria’s Secret as she looked through their swim suit collection. 

 

“Ok the next dilemma is color. What color will look good on you? Black is always great so maybe we should get you two bikinis. A black one and something else,” Ama wondered as she roamed the aisles. Ama looked back and saw the bored look on Rory’s face.

 

“Girl you have to help me out here. I know you’re stressed out with having a project for Truncheon but you also have to find a bikini before you leave Friday morning. So how about we do this and then we take a walk and talk it out. Maybe some brainstorming will help you out.”

 

Rory took a deep breath. “I guess so. Only if we can get a milkshake or some ice cream though.”

 

“Oh no doubt Gilmore. Now pick a color, hot pink or purple,” Ama held up two different bikinis and Rory made a disgusted face.

 

“Neither...those colors don’t look good on me. Look for something...blue,” Rory ordered.

 

Ama rolled her eyes and put away the bikinis and continued to look through the racks. “So hey you didn’t get to tell me how home in Stars Hollow was. Everything cool with your mom?”

 

Rory smiled at the question, knowing that after their movie binge of The Godfather series they were definitely going to be ok. They’d also talked at least once a day all week since she got back to Philadelphia. “Things are great actually...I think we have a good understanding now and she’s actually going to try and not judge me so much about my choices.”

 

Ama snorted. “How’s that working so far?”

 

“Pretty good actually! She defended me when my ex boyfriend’s wife yelled at me for making out with him before I came here. It was pretty embarrassing. She was also pretty helpful when Jess and I got into a fight.”

 

“Woah, wait the wife found out about that? What did you do? Did the ex come to see you?”

 

“Well yeah it was pretty horrible. And Dean did come to see me but what he got was an eyeful of me and Jess post coital...or well waking up after all that.”

 

Ama’s eyes looked like her eyes were going to pop out of her head. “Ok back up, Jess came to Stars Hollow?”

 

“Yes!” Rory exclaimed with a dreamy expression. “I called him crying and he was really worried so he drove up to make sure I was ok.”

 

Ama smirked. “And then you guys had sex all night.”

 

Rory blushed. “Hey!”

 

Ama waved her off as she picked up another bikini, “Oh come off it Rory you guys are nuts. Oh yeah how did that whole thing with you giving him a hand go? I feel like I need all these updates!”

 

“Ama! Why do we always discuss these things in public?”

 

“Ok if there’s one place we can talk about sex I think it’s Victoria’s Secret. Now come on! Details.”

 

“I did ok! He seemed to like it.”

 

“Hand or mouth?”

 

“Ama!”

 

“Answer the question Gilmore!”

 

“Ugh...hand.”

 

“Good start! When are you gonna try mouth?”

 

“You are the worst,” Rory hisses. “I'm not telling you that here. Why are you asking?”

 

“Because Jess will do whatever you want whenever you do it I swear.”

 

“Ok I’ll think about it, can we stop talking about this? Oh look the bikini you’re holding is pretty,” Rory says to distract Ama. She’s not lying though. Ama holds up a royal blue string bikini that Rory is sure will brighten her fair skin and bring out her eyes. It’s the best possible scenario for her wearing a bikini.

 

Ama nods in approval and hands the bikini to Rory. “Now we must find you something black! And a cover up. Get hurrying Rory, I need a milkshake!”

 

Rory laughs. “You’re really bossy when you’re shopping Ama.”

 

Ama rolls her eyes. “Nah if I leave you to your devices, we’ll be here forever. We’ve got things to do!”

* * *

Rory and Ama walk casually along the street heading towards Love Park. They sip casually on some milkshakes and try to come up with ideas for Rory’s Truncheon project.

 

“I mean it definitely has to be something to do with the city. What if it was something like the big city from a small town girl’s perspective?”

 

“Well sure, but that’s been done a lot. How would it be unique? How it would it bring out your voice?”

 

Rory thought for a moment before moaning in frustration. “This is impossible, I’m never going to think of something!”

 

“Ok you need to calm down, stressing out like this isn’t going to be helpful for you thinking of something. You should come to yoga with me, you could use an outlet to clear your mind.”

 

“Gilmores don’t exercise.”

 

“Just once! It can hardly be called exercise. Also it makes your body crazy flexible and Jess will love that.”

 

“It always has to come back to this with you doesn’t it?”

 

“Dirty mind Gilmore,” Ama taps her head with a grin.

 

Rory giggles and shakes her head. For all her protesting, she can admit that Ama makes her open up and she’s one person she knows will not judge her. She certainly can’t ask her mom, Paris, or Lane any questions about sex. Ama is a perfect blend of fun and nonjudgmental to handle those conversations.

 

The two girls entered Love Park and were immediately confronted with a blend of people walking and running around, taking pictures in front of the sculpture, and kids running around in the flowing fountain. Both girls smiled and Ama took her camera out of her bag and took a picture.

 

“This will be great for my photo project. I don’t know why I didn’t come here before!”

 

“Which photo project is this?”

 

“Philadelphia Summer. I think this city is at its best in the summer. Everyone is out and the buildings are bright! I don’t know where I’m going to present it but it’ll be cool. None of it in black and white or anything. Too many vibrant colors to capture.”

 

“Yeah the red of the sculpture will pop so much against the water,” Rory observes. “That’s a really great idea, maybe we can do an exhibit of it at Truncheon for the Summer Open House?”

 

“Yeah! I can totally get it done by then. Do I need to talk to Chris?”

 

“Yeah, come to Truncheon tomorrow and we’ll present the idea to him Bring some sample photos.”

 

“Thanks, girl! That’ll be fun.”

 

The girls stood for a few minutes observing the fun happening around them. Rory smiled seeing a little girl soaking wet run out of the fountain to hug what seemed to be her young mother who looked obviously annoyed that she was wet, but the smile creeped up on her face. 

 

“You know what’s funny about Philadelphia? Everyone always made it seem so scary before I came here. I think they do that with most cities, but especially here. I remember when I got here and I had to take the broad street line to go find Jess and I was terrified because I’d never been around so many people in my life like that. But everyone was actually really nice and helpful when I looked super lost...I was surprised.”

 

“City of Brotherly Love for you,” Ama agreed.

 

Rory nodded and continued to look around. They walked closer to the sculpture when a red headed woman came up to them with an eager face. 

 

“Sorry to bother but would one of you mind taking a picture of me and my fiance in front of the sculpture?” Rory smiled and took the camera from the woman, placing herself in a position to get a good picture. She watched as the woman ran up to her fiance and wrapped her arms lovingly around his middle and he gazed down at her with a smile. Rory quickly captured the moment and took another couple pictures so they would have some options. As she watched them, she had a thought and decided to voice it as she handed the camera back to the woman. 

 

“Hey could I ask you a question?” Rory asked. The woman and her fiance nodded and took their camera back from Rory.

 

“Are you each others’ first loves?” Rory asked curiously. They both furrowed their eyebrows and looked at each other. 

 

“Well,” the woman started. “Actually he’s my first love. We met after I graduated from college and I’d had a couple boyfriends but it was never anything serious. And then we met and it just..fit.”

 

“She’s actually not my first love. I had a serious relationship during high school into college but it ended up not working out and it was pretty devastating. But I met her and yeah..it fit. So I think she’ll be my last love and that’s what matters.”

 

Rory gave them a small smile. “And knowing that there’s been someone before you doesn’t bother you?” she asks the woman. She shakes her denial. “He’s right...he’s always been honest and he’s always loved me right. I don’t need to worry.”

 

Rory thanked them and asked if she could take a picture with Ama’s camera. “I’m doing a project for the Truncheon Zine on love in Philadelphia and I think you guys would be great for it. If you don’t mind I’d love to use your picture and the quotes you gave me?”

 

The couple agreed and took another picture. They even offered to send Rory the pictures she originally took of them. They exchanged emails and Rory thanked them for their time.

 

“I think I have it,” Rory commented in wonderment. “Think about it, how many people do you see come through this park all the time just to take a picture in front of this sculpture? But who knows how they’re connected? If they’re married, in a relationship, family, friends? What’s a piece of the puzzle that leads them to taking a picture in front of a sculpture that says love?”

 

“It’s an interesting thought. But what does that look like?” Ama wondered.

 

“Well, I come here and I offer to take pictures of people in front of the sign in exchange for getting to ask them a question and putting the in the zine. The point is tell stories you know...what does love look like around here?”

 

“Love in the time of Philadelphia!” Ama mused.

 

“That’s a good name! I might steal that.”

 

“I can help with pictures sometimes if you want?” I wonder how good it would look if you even got some of the people that sit around here, the kids in the fountains, the people who eat their lunch. I can try and take a picture that includes a backdrop of the sculpture? And you handle the questions!”

 

“That would be amazing,” Rory beamed, taking Ama’s hand in gratitude. “Who knew those morning talks with Jess would be so helpful?”

 

“What do you mean?”

 

“Jess and I have this thing where we just..talk in the morning. And we always ask each other questions but Jess says the ones I ask him are kind of random. Questions about things he doesn’t really think about. Like one time I asked him if he thought his mother had ever been in love?”

 

Ama laughed. “That is random. What did he say?”

 

“Well he gave me a good answer, it told me a lot about him. I probably shouldn’t tell you because it’s personal for him.”

 

“That’s fair.”

 

“But I ask him those questions because I’m really curious about him and what makes him tick you know? I don’t want to ask these people those silly generic interview questions, I’m so used to doing that.”

 

Ama gave Rory a knowing look. “You guys are really sweet. He seems to be really good for you.”

 

Rory nods. “He is. Now come on!” Rory takes Ama’s hand and starts to lead her out of the park. “We have to go to Truncheon and present this all to Matt!”

* * *

Rory walks into Jess’s apartment at the end of the day with a triumphant grin on her face. She enters the living room to see him quietly sitting on the couch reading a book. He looks up and raises an eyebrow at Rory’s expression.

 

“Someone looks like they won the lottery today,” he comments sardonically.

 

Rory rolls her eyes but keeps her smile. “You’re not ruining this with your writer’s block attitude sir, Matt told me you left early today to try and write. It obviously didn’t go well. But I had a great day! I figured out my project!”

 

“Oh really?” Jess bookmarked his page and put his book down to give Rory his full attention. “Let’s hear it.”

 

“Love In The Time of Philadelphia,” Rory explained with a dreamy look. “I’m going to take pictures of people in Love Park and ask them questions...kind of like I ask you questions.”

 

“So random and deceivingly personal?”

 

“Exactly! It works to pull at a hidden layer in this city. It’s full of love even though everyone who isn’t from here doesn’t think that! Love Park is the perfect place to explore that!”

 

Jess cracks a smile, his dark mood lightening at how excited Rory is. “I’m glad you’re really excited about this, I was worried for a moment there.”

 

“Yeah?”

 

“You’ve been in a sulky mood. Working hard though. I thought you would figure it out on your own though.”

 

“Because I’m a smart, capable, and independent woman huh?” Rory giggles and sits next to Jess, wrapping her arm around his waist and propping her chin on his shoulder. 

 

“Yes that’s exactly what you are,” Jess smirked. The two of them laughed and Rory kissed Jess’s neck softly. 

 

“Are you ok? You seem to be in a mood?” Rory murmured.

 

Jess shrugged. “I just can’t get the story to work. Reaching a breaking point here. I mean Chris and Matt haven’t put a lot of pressure on me to get this done but I feel the pressure. I’m thinking about it too much.”

 

Rory frowned and gave Jess’s neck another kiss. “I’m sorry. Maybe the beach will be helpful? Getting away for a bit? We’ll work really hard on it.”

 

Jess hmphed in response. Rory reached up and kissed Jess’s cheek. “Sad boy. You were so excited about the beach.”

 

“I am it’s just...I don’t know.”

 

“Will it make you feel better if I told you I got two bikinis today while I was out shopping?” Rory saw a hint of a smile.

 

“A little,” Jess admits. 

 

“I really like them so don’t think I did it for you,” Rory says while tracing circles on Jess’s chest. She continued to cuddle up to him, raising her legs so that they would sit in his lap. He turns his head to look at her and gives her a soft kiss, wrapping his arms around her to bring them closer. 

 

“That definitely raises the anticipation levels,” Jess hums.

 

“Well good, because I want to make you feel better,” Rory whispers against his lips. She kisses him and gently takes his cheek in her hand. The kiss deepens and Rory bites Jess’s lower lip lightly to get a pleased response out of him. He smiles into their kiss and grabs Rory’s bare thigh, kneading her inner thigh slowly up to the hem of her skirt.

 

“All that excitement make you wet Rory?” Jess whispers once he breaks their kiss. Rory’s breath hitches and she moans in anticipation, arching her back. Jess reaches her panties and can feel the wetness seeping through. He smirks against her neck as he kisses and nibbles his way up and down. “Fuck, you are wet,” he says hoarsely.

 

Rory moans in response and Jess takes his hand from beneath her skirt. He gently takes Rory’s legs off his lap and tries to widen their stance so he has better access. At this movement, Rory’s eyes pop open and she closes her legs despite Jess’s attempts to open them.

 

“Wait...Jess wait,” she puts her hand on his, moving it back onto his own lap. “I want...I want to do something for you. I’ve been thinking about it.”

 

“What?” Jess says bewildered. 

 

Rory sits up and moves to straddle Jess’s lap, taking his face in her hands and giving him a hard kiss. “Tell me how to go down on you,” she whispers against his lips. Jess’s eyes widen in response. 

 

“Rory you don’t...you don’t have to do-”

 

“I want to,” she says firmly. “You’re so giving all the time and I want to do this for you. I want to make you feel better,” she tells him shyly and softly grinds into his crotch. She can feel him hardening beneath her and she groans leaning her head back. Jess latches onto her neck, sucking the pulse point and making her shudder in enjoyment. His hands roam her body, one squeezing her waist underneath her shirt and other reaching beneath her skirt and squeezing her ass. He pushes her harder against him, spurred on by her request. 

 

“Let me make you come first,” he says against her collarbone before taking a lick.

 

“No,” she moans. “You first this time, I want you first for once.” She pushes him away from her and slips her shirt off gaining more confidence under the weight of Jess’s clear desire for her. “You’re very distracting,” she scolds. She takes off her bra and gets up before Jess can it any further.

 

“Take off your pants,” she orders while she reaches under her skirt to take off her panties. Jess complies quickly, unbuttoning his jeans and slipping them off to his feet and taking off his shirt for added measure. Rory bends down to her knees and takes Jess’s pants off the rest of the way for him while he gently runs his hands through her hair. She scoots to get in between his legs and runs her hands up and down his thighs. She looks up to him with big doe eyes that take Jess’s breath away.

 

“This is what you wanted right? On the phone last week,” she asks. “You said you couldn’t wait to teach me how to suck your cock. Me just wearing one of my cute skirts and on my knees for you? I want to give that to you...so teach me.”

 

She takes hold of his cock at the tip, rubbing her thumb over the tip and spreading his pre-cum down to the base. She licks her hand and gently squeezes him from base to tip, earning a guttural moan from Jess. “Fuck, Rory.”

 

“You said you would teach me Jess but you’re not saying anything,” she says to him innocently. “I can’t do anything if I don’t know what to do.”

 

He lets out a breathy laugh and gently takes Rory’s cheek, leaning her mouth closer to where he wants it most. “You sure, Rory?” he double checks.

 

“I want to,” she confirms and licks her lips. 

 

“Put your mouth on the tip,” he instructs. “Just suck on it.” Rory nods and maintains eye contact as she puts her mouth tentatively around the tip of his cock. She takes a taste, swirling her tongue around the tip, cheeks reddening at how dark Jess’s eyes become. He whispers his approval and she keeps going, exploring his cock with her tongue and lips, placing licks and kisses up and down. Jess pants and leans his head back unable to look any longer without fear of blowing suddenly. 

 

“God, Rory you’re such a tease,” he groans. “Put your mouth on me, put as much of me as you can in your mouth.”

 

Rory looks up at Jess’s pained expression and raises an eyebrow. She takes a deep breath and proceeds to put her mouth around him again, moving her head down his cock and wrapping her hand around the base to ground her movement. Jess hisses. 

 

“Watch out for teeth,” he warns. “Hide your teeth.”

 

She takes note and focuses her lips around the skin, hiding her teeth behind them so as not to harm him. She swirls her tongue around him and breathes hard through her nose. She closes her eyes and brings her head back up, pursing her lips around the tip again and earning a strained moan from Jess. 

 

“Fuck that’s good, keeping doing that,” he encourages. “Just bob up and down like that.”

 

Rory continues this motion to his delight, taking her time to slowly bob up and down around Jess. Both of her hands are kept busy, one stroking around the base of his cock and the other pressing against his inner thigh. She kept at it for another minute before coming up for air, thankful that her eating habits had taught her how to breath through her nose properly while she stuffed her face with food. 

 

“Rory,” Jess groans. “I need...fuck.”

 

“Tell me,” she says before placing a kiss against the base of his cock, running her hand up and down in a circular motion she knew worked for him so she could give her mouth a break. 

 

“Oh god keep doing that with your hand just...my balls can you do that?”

 

Rory looks down to the referred area and blushes, not quite expecting this to be part of the deal. “What?”

 

“Just...keep doing that with your hand and put them in your mouth it’ll finish me off. But if you don’t want to just...get the condom out of my pocket and get up here. Either one.” His head is still thrown back, eyes closed in tortured ecstasy.

 

Rory looks down again and takes a deep breath, determined to finish what she started. She could take the easy way out and just get the condom so that they could both finish but Ama was right about this-Jess was completely powerless to her and she kind of liked it.

 

She closed her eyes and wrapped her mouth around his sac, sucking at the same time she flicked her wrist faster around his cock creating an unbearable shock of pleasure through Jess’s system. 

 

“Oh god Rory keep going. Fuck, you’re amazing.”

 

He’s getting closer and he trembles, panting and muttering curses. And when he reaches his peak he comes on his stomach, Rory slowing down her hand’s movements around him and slipping her mouth off his sac. She looks up at his cock curiously wondering what his cum tastes like and takes a hesitant taste around the tip. Jess hisses a “fuck” before slumping against the couch. Rory lets go of his cock and reaches for the tissues on the table next to the couch. She cleans off his stomach and looks up at him nervously. “Was that what you wanted?”

 

Jess gazed at her with a soft reverent expression. Was it the best he’s ever had? No honestly. But her enthusiasm brought him to the brink faster and harder than any other girl ever had.

 

“Get up here,” he ordered. He took her hand and pulled her until she landed back in his lap in her original position straddling him. He kissed her softly and reached under her skirt with one hand find her clit, finding that she was more aroused than when they first started. 

 

“Did you like doing that baby? God you’re so wet,” he observed with a grin. She blushed and hid her face in his neck, leveraging her hands on his shoulders to grind against his hand. 

 

“You’re unbelievable,” he compliments. “You know that?” He enters her with two fingers easily and immediately starts a rough and fast pace, using the heel of his hand to rub against her clit. Rory’s hips move in sync with his hand and she keens against his neck. Jess rubs his hand up and down her back and kisses her neck softly. 

 

When she comes it’s with a loud shriek and Jess gently takes the nape of her neck in his hand so that she’ll look at him. He keeps eye contact with her through her orgasm, softly rubbing against her pulse point. She whimpers against his lips once she comes down and he removes his fingers, wiping them on her leg. He gives her a series of short kisses and smiles against her mouth.

 

“How the fuck am I supposed to let you go in August huh?” he whispers. She doesn’t answer, because she doesn’t know either.   
  


**Notes for the Chapter:**

> I gained some inspiration for Rory’s project from things like Humans of NY, so I hope that gives you all an idea of what she’s going for with this!


End file.
